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Bowery Capital Startup Sales Podcast

Bowery Capital is an early stage venture capital fund that focuses solely on helping portfolio companies with sales related challenges. This podcast is a discussion between the Bowery Capital team and experienced industry friends in an effort to help a younger generation of startups better understand the issues and pain points they will face when thinking about early revenue generation.
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Mar 30, 2018

This week, the Bowery Capital team hosted Zach Sims, Bowery Capital Venture Partner and CEO of Codecademy, to discuss "Selling Software In Education." Codecademy is a New York, NY based education software company focused on teaching the world how to code. The company is committed to building the best learning experience inside and out to ultimately create the online learning experience of the future. When you think about sales in specific industries, selling software in education is probably one of the more challenging industries. Buyer inertia is real, pricing is always very unique to the ICP, competition is fierce, and the fragmentation especially in the K-12 market is enormous. On the podcast this week, we covered selling software in education with Zach Sims. Zach knows a thing or two about the topic having grown a freemium product to 40MM users with hundreds of thousands of people using the product daily. He’s sold into K-12, Corporations, Governments, and other areas of education. We kicked off the podcast talking about Zach’s background and how he was able to get the idea for Codecademy. We also spent a bit of time talking through the launch of the product. From there, we dug in around how Codecademy sells their product today and how specifically they feel about software sales in education overall. Zach had a good comparison around this ICP (hint: it’s like a gym membership) and why it really is so challenging to build a big business in the space specifically because of the ICP. We then moved on to some of the assumptions the Codecademy team made that turned out to be right or wrong relative to their start. Third, we covered some of the models in market today such as free, freemium, inside or outside sales driven and what tends to work and what does not. We then played a bit of round robin and talked through the many sub categories of the industry and what Zach thinks about success or failure when thinking through selling software in education. We close with some philosophy about why the space has not seen a ton of success beyond the legacy LMS players (i.e. Skillsoft, Cornerstone OnDemand) and then some new entrants in the content space (2U, Lynda). Zach closes with some final tips and tricks around software sales in education. Overall it was an informative and educational podcast! Zach Sims is the CEO and Co-Founder of Codecademy, helping people advance their careers by teaching highly sought after technical skills. On top of that, Zach is also a Bowery Capital Venture Partner. Prior to Codecademy, Sims worked at .406 Ventures, GroupMe, AOL Ventures, and Drop.io in various roles, including consulting and business development. Zach graduated from Columbia University with a degree in Political Science.

Mar 29, 2018

This week, the Bowery Capital team hosted Amber Banks, Director of Sales Training and Enablement at Justworks, to discuss "Building Diverse Sales Teams." Justworks is an online platform that handles the payroll and payments procedure, benefits facilities, and compliance issues of its users. Recently, Justworks closed on a $40mm Series D funding round led by FirstMark Capital with participation from existing investors, Index Ventures, Thrive Capital, Bain Capital and Redpoint Ventures. On this podcast, Amber and I discuss how technology has changed the landscape for women in sales in recent years and the importance of awareness early on when building a diverse workforce. Amber discusses her journey to sales, the importance of building personal brand early in your career, and explains that companies should be sure to show a career path for women in order to attract great talent in the first place. She emphasizes the importance of having women in the interview loop, on your board, and in the C-suite to ensure that there is buy-in around diversity and inclusion from the top. We chat through best practices for retaining great talent once it’s in the door, ways to build out D&I initiatives internally and awareness around unconscious bias. Amber Banks is the Director of Sales Training and Enablement with Justworks and is passionate about building high impact sales organizations and helping salespeople reach their full potential. She has spent more than a decade scaling high growth technology companies in New York and San Francisco and many of the reps she has coached have gone on to build top tier sales and recruiting teams. She’s very active in diversity and inclusion initiatives within Justworks and the broader community, supporting organizations like SHE CAN and Defy Ventures.

Mar 15, 2018

This week, the Bowery Capital team hosted David Appel, Head of the SaaS Vertical at Sage Intacct, to discuss "Building Your SaaS Dashboard." Sage Intacct is a provider of cloud financial management and accounting applications. Resulting from Sage’s acquisition of Intacct in mid-2017, the company serves thousands of businesses in growth and enterprise markets. With ~$100MM in ARR and growing 30%+ year-over-year, Sage Intacct is an emerging SaaS market leader with decades of experience helping businesses understand their goals and metrics. Here at the Bowery Capital Startup Sales Podcast, we’ve hosted at least 10 episodes around the topic of SaaS metrics over the years. But understanding the various metrics is only half the battle. Today we discuss the other half: choosing the right ones for your business, understanding where should be on each, and organizing your tracking efforts in to an actionable SaaS dashboard. David begins by walking us through the major categories of KPIs you’ll think want to think about as a startup leader. We bring some context to these metrics by then walking through real-world growth companies and their numbers for each, from deep enterprise to high-volume examples. We then explain how to build your SaaS dashboard by picking measures commensurate with your stage and what you are trying to prove, be it product fit, scalability in the market, or financial soundness. Finally, David also shares some insight into the tools his clients use for SaaS dashboard exercise, Sage Intacct and otherwise. You can find a presentation that David was kind enough to share with us on this topic embedded below; it provides visuals fleshing out many of the talking points covered in our show today. We hope these resources combined will serve as a helpful guide on performance management planning for SaaS leaders at any stage. David Appel is Head of the SaaS Vertical at Sage Intacct, where he oversees Product, Marketing, Sales, and Implementation for the Company’s largest vertical. Prior to Sage Intacct, David served as the Head of Direct Sales at Bill.com, where he grew business by 85% and tripled the team over his 18-month tenure. Previously, he held various sales leadership roles at leading software companies including NetSuite, IBM and Oracle. Having spent over 10 years as a startup sales advisor, David has helped many founders think about their own SaaS dashboards directly.

Mar 2, 2018

This week, the Bowery Capital team hosted Jordan Rackie, Chief Revenue Officer, and Ellen Kindley, VP of Business Operations, of QASymphony to discuss “Go-To-Market Kick Off vs. Sales Kick Off.” QASymphony helps companies create better software by being the only provider of truly enterprise-level agile testing tools. On the podcast, we discuss why the team at QASymphony decided to do a Go-To-Market Kick Off this year as opposed to the more traditional Sales Kick Off that they’d done in years past. They dive into how the Go-To-Market Kick Off was structured from a timeline and activities standpoint and what teams were included in the day. We then discuss how the various leaders of the sales, marketing, and customer success teams presented 2018 goals. We end by walking through learnings from the day, things that others who are considering doing a Go-To-Market Kick Off should plan for, and their plans for next year’s event. Jordan Rackie is the Chief Revenue Officer at QASymphony, responsible for leading all new revenue acquisition (sales and marketing), generated from both new and existing customers. Jordan represents the new breed of technology go-to-market leaders. His leadership in the SaaS space, which includes a vast understanding of the latest sales and marketing enablement tools, provides a strong foundation that will help QASymphony scale and grow the business. Jordan was one of the original sales leaders at Pardot, helping the marketing automation company grow from a few thousand dollars recurring into an organization that eventually sold for near $100 million, and is now owned and operated by Salesforce.com. Following success at Pardot, Jordan directed sales process and growth at PeopleMatter, a venture-backed organization (Noro-Moseley, StarVest Partners, etc.). While at PeopleMatter, Jordan inserted sales strategies that directly contributed to a 700%+ increase in quarterly bookings. A native of Georgia, Jordan holds a Bachelor of Science degree from the Georgia Institute of Technology. Ellen Kindley is a dynamic business operations leader at QASymphony specializing in sales process, data management & analytics, strategy and sales tech. Ellen seeks to enable growth by facilitating strategic planning, infrastructure and overall go to market excellence. Ellen is passionate about laying the foundation on which SaaS startups can scale and grow - always striving to be the driving force for productivity improvement. Starting at QASymphony in 2014, first as a consultant and then as a full time employee in 2015, Ellen has successfully set the stage for hyper growth. Every step is data driven as she sets initiatives and priorities, evaluates gaps and executes improvements. Ellen's goal everyday is to allow sales management and individual contributors to focus solely on revenue generating activities. Ellen holds a B.S. in Accounting and Legal Studies from the College of Charleston in Charleston, SC.

Feb 21, 2018

This week, the Bowery Capital team hosted Jeanne DeWitt, Head of Sales for US and Canada at Stripe, to discuss “Team Structuring In Transactional Sales Organizations.” Stripe is a technology platform that developers use to build internet businesses. Thousands of businesses – ranging from startups to Fortune 500 companies – rely on Stripe’s software tools to securely accept payments, expand globally, and create new revenue streams. Stripe users include Twitter, Kickstarter, Shopify, Salesforce, Lyft, and many more. On the podcast, Jeanne and I begin talking about her background from Google, Dialpad, and now Stripe and specifically how those organizations were designed. We then moved on to describe what we all mean when we talk about “transactional” sales organizations so the listeners could understand our overall point of view. From that point, we covered how Stripe is designed from an organizational standpoint and how it differs in terms of SDRs (none), AEs, and CSMs. We also talked a fair amount about other organizations and thinking through when to move away from “self-serve” to something like transactional selling. Jeanne also gave the listeners some points of view on how she and the founders approached sales two years ago (remember Stripe was very successful with their self-serve model), noting how this conversation can go very right or very wrong when your self-serve product is high velocity and working well. We then talked about what metrics are necessary to move from self-serve to anything more upstream from a selling standpoint. When to hit the gas and when to maintain the current state is really important and Jeanne gave great tips from her pattern recognition over a long career. She feels that people tend to move up too early and talked a lot about the math necessary to do this. We close on hiring and celebrating wins in organizations that are primarily transactional. Overall, it was a wonderful podcast and Jeanne has had an exceptional career with lots of knowledge to share. Jeanne DeWitt is the Head of Sales for the US and Canada at Stripe. Prior to joining Stripe in 2016, she was the Chief Revenue Officer at Dialpad. Before that, Jeanne held multiple sales leadership roles at Google, including serving as Director of SMB Sales for North & Latin America and Head of Google Apps SMB Sales for Japan & Asia Pacific. Jeanne studied Markets and Management, as well as French and Spanish, at Duke University before going on to receive her MBA from Stanford University.

Jan 26, 2018

This week, the Bowery Capital team hosted Ralph Barsi, Global Sales Development Leader at ServiceNow, to discuss "Effective Communication at Scale." ServiceNow is a cloud computing company, based in Santa Clara, CA. ServiceNow’s applications automate, predict, digitize and optimize business processes and tasks, from IT to Customer Service to Security Operations and to Human Resources, creating a better experience for your employees, users and customers while transforming your enterprise. On the podcast we discuss the importance of maintaining effective communication within an organization and tactical steps that companies can employ to become more structured in their communication with employees. As your SaaS business and particularly your sales team grows, both the frequency and cost of employee miscommunication escalate. Thankfully, Ralph is here to break down the common pain points SaaS businesses face and offer some suggestions for you to create more effective communication channels within your teams. Ralph walks through the end-to-end process of creating a successful communication plan, including creating objectives, implementing the plan, and tracking progress against those objectives. We dig in on the right time in a company’s life to implement structure around your communication, and the right tools to use for implementing and tracking your communications at scale. Ralph Barsi is the Global Sales Development Leader at Silicon Valley-based ServiceNow, where he leads teams of account development representatives in 11 cities across the globe. Ralph regularly speaks and writes about sales and leadership and is recognized among the top inside sales leaders in the technology industry. Ralph also serves on the Board of Directors of The Gable Heart Beats Foundation, a non-profit organization whose community of musicians, athletes, entertainers, and influencers raises awareness of heart diseases and helps save lives.

Jan 19, 2018

This week, the Bowery Capital team hosted Jack Altman, Founder & CEO at LatticeHQ, to discuss “Testing SaaS Payment Terms.” Lattice is a platform for employee-centric performance management. The SaaS offering enables easy management of 360 performance reviews, OKR / goal setting & tracking, real-time feedback, and 1-on-1s, amongst other workforce management functions. In today’s show, we’ll talk through Jack’s early thought processes around pricing and outline methods any founder can use to pressure test his or her SaaS payment terms. Today, Lattices’s sales engine is humming along: Lattice now serves over 400 customers including Coinbase, PlanGrid, Cruise, and Birchbox. In earlier days, things weren’t so easy. To begin with, the Human Capital Management software space is a crowded one. Fragmentation is especially intense in Lattice’s category, Performance Management. From full-stack solutions to lite, freemium, or even free SMB-oriented tools, Performance Management offerings vary widely in terms of features and sophistication. This diversity of choice makes zeroing in on the “right” pricing model or payment terms that much more difficult, with so many disparate competitors to frame against. As Jack also learned that SaaS payment terms and pricing have to be tailored to align with customer value. Like many enterprise software products, Lattice works best when an entire organization is committed. In the case of performance management specifically, input and engagement from employees and managers is a must-have; garbage in, garbage out. Through testing, Jack found that low pricing schema, highly flexible SaaS payment terms, and long trial periods—common in SaaS HR tooling—failed to reinforce this user buy-in. Without sufficient time and resources committed, the system was undersupplied with data, and hence too many customers reaped the rewards of Lattice’s full value. Interestingly, only by increasing the ask to adopters upfront was Jack to maximize value discovery for his users. As Jack will discuss, he spent a lot of time A/B testing various SaaS payment terms in particular streamline time-to-value. By iterating on these levers, he was able to better optimize the company’s sales funnel for max user benefit, reducing CAC and driving top-line growth simultaneously. Jack Altman is CEO of LatticeHQ, which he founded in late 2015. Since then, the company has raised nearly $10MM, most recently closing a Series A led by Thrive Capital and joined by insiders Slack and Y-Combinator. Prior to Lattice, Jack served as VP of Product at Teespring. Before that he was a Seed investor at Hydrazine Capital. Jack started his career as an investment banking analyst with Gleacher & Company, after earning a BA from Princeton University. With experience in management, product and finance, Jack is a perfect guest to join us in exploring SaaS payment terms. Happy listening!

Dec 21, 2017

This week, the Bowery Capital team hosted Scott Gifis, Vice President and Managing Director at AdRoll, to discuss “Mapping and Selling Into New Markets." On the podcast we discuss different techniques, strategies, and measurements that SaaS companies need to consider before they sell into a new geography, to a new type of buyer, or even as they consider an account-based strategy where they’re selling new products into existing relationships. In the record business, there’s a saying that “you have all your life to write your first album, and only 18 months to write your second." Similarly, in SaaS, you have a lot of time to map your first market and product you’re going to sell, but once you’re initially successful and tap out your first segment of a market, you’ll be under pretty quick pressure to find new markets to sell into, or additional products to sell to your existing customers. In today’s podcast, Scott breaks down all the things you need to do, and more importantly perhaps, the things you shouldn’t do, to successfully figure out new markets and buyers you’re approaching. Whether you’re an early stage company going through the repetitions of testing out markets, or a software behemoth figuring out where to go next to maintain blistering growth, there are tips, frameworks, and questions to ask which will guide you in the right direction. We talk about everything from Arm & Hammer’s strategy decades ago, to AdRoll’s account-based sales and marketing strategy today on ways to explore and execute on new markets. Scott Gifis is the VP of North America and Managing Director at AdRoll, where he’s seen (and led) massive growth of their sales and products over the past 4 years. Scott also has a few fun facts: he once wanted to be a pro hockey player, and promised his dad that if he would let him play Juniors Hockey, he would get some practical business experience too, which led Scott to join a VC early on and ultimately follow a path into SaaS. Scott also enjoys spending time with his three daughters at home to balance his day-to-day at a rapidly growing company that just moved to a bigger office here in NYC. Next up, we might have to pick Scott’s brain on work-life balance tips!

Dec 14, 2017

This week, the Bowery Capital team hosted Dean Onishi, Director of Documentation and Certification at Procore, to discuss "SaaS Certification Programs." Procore is a cloud-based construction management software application built for the construction industry professional, striving to make project management effortless, one task at a time. With Procore’s easy-to-use and collaborative software, users can manage their projects at anytime, from anywhere, with any Internet-connected device. During this week’s episode, Dean walks through the concept of SaaS certification programs and how they can be influential in complementing a business’s existing value proposition. Dean is keen to share anecdotes and best practices from his time at Procore. While a lot of companies attempt, in earnest, to create these programs, they fail to implement effective programs. Dean illuminates on the major hurdles in rallying a company and users, alike, around embracing SaaS certification programs, and he shares with us a few companies that he believes are doing this well. Certifications are a proven incentive scheme to increase engagement across an industry, particularly in a historically offline ecosystem like construction. Further, Dean talks to us about how the integration of a SaaS certification program can cultivate a vibrant community of users with powerful network effects. Dean takes us through the obvious, direct benefits of such programs, as well as some of the less obvious ones, like driving SEO traffic to your site. SaaS certification programs are most appropriately a part of the later-stage product roadmap, once certain customer milestones have been met. Therefore, Dean offers ways to assess appetite for adding a certifications program with existing customers. Conversely, Dean talks about organizational approaches to installing and maintaining such a program. In addition, Dean suggests relevant mediums for delivering the curriculum behind certification programs. Lastly, Dean defines a metrics-driven framework to evaluate success in a certification program. In lieu of building your own program, Dean recommends a few alternative, third-party resources to pursue to launch your own certifications capabilities. Dean is the Director of Documentation and Certification at Procore. He has been in this role for over a year and was previously a Technical Publication Manager at Procore for several years. In Dean’s current role, he is responsible for driving successful user adoption of the Procore platform by providing users with helpful support documentation and training materials to “self-serve” all of their educational and training needs. Dean manages the Documentation team that runs Procore’s Support site and Procore’s Certification program.

Dec 7, 2017

This week, the Bowery Capital team hosted Donya Rose, Sales Compensation Consultant for Xactly, to discuss "Building Winning Sales Compensation Plans." Xactly is a market leader in on-demand sales performance management. The company’s SPM Suite of products, enables sales and finance executives to design, implement, manage, audit and optimize sales compensation management programs easily and affordably. Xactly’s solutions automate the process of aggregating data from disparate systems into a secure, hosted repository, and enable companies to leverage this business data, which is the lifeblood of sales performance management. In this episode, Donya walks us through the do’s and don’ts of building rewarding and sustainable sales compensation plans for SaaS businesses. Donya begins by breaking down the 2 basic principles for having a well-structured compensation plan: motivation and focus. She explains that compensation plans can often be an arms race, especially if you try to match survey data that can be found on Glassdoor or other sites because the numbers are inflated. Instead, she recommends that companies analyze their own metrics and set realistic goals based on what their current team is hitting.  She then goes on to explain the importance of “Right Pay Level” and “Right Pay Mix,” meaning the way that you split compensation between base and commission (OTE). She emphasizes the importance of having only a few measures make up someone’s OTE (she warns against having more than 3 and explains that having only 1 measure is truly ideal.) She goes on to explain that with a typical SaaS model for new business closers (Account Executives or Enterprise Account Executives) who are on a 50/50 split (50% base, 50% OTE) plan, your truly outstanding reps should be earning 2-3X the target incentive, creating a genuinely rewarding plan for those who overachieve. In the spirit of creating meaningful upside, we then discuss the importance of creating uncapped commission plans. Donya explains that she does advocate for appropriate controls for “runaway payments” and gives a few examples of the best ways to approach building a plan like this and explains her model for “Deceleration Over Excellence,” a concept that was new to us here at Bowery. She encourages founders or hiring managers to truly incentive their reps by putting as “juicy a rate” right over quota as possible to incentivize reps to overachieve but then describes a maintainable model for achievement over 150% to goal. We also dive into building compensation plans for first sales hires when there is limited data at the founder’s disposal and the different metrics that need to be monitored to ensure a reliable model. Donya highlights that even with a flat line compensation plan (meaning there is a flat percentage payout no matter the size of the deal or attainment to quota) it’s imperative to have a change in the compensation structure once a rep hits quota, otherwise the quota itself becomes irrelevant. Donya finishes by explaining that the deal cycle and contract length are two other vital factors when considering a compensation plan and payout structure. We also touch on the cadence and best practices for updating and changing compensation plans. Donya Rose has over twenty-five years experience in leading the design and implementation of systems and processes to ensure alignment of sales results with top business priorities. She has led projects in sales target setting, measurement and forecasting, technology enabled selling, and sales compensation plan design. Today Donya focuses primarily on sales compensation plan design, and has designed hundreds of sales compensation plans since that became her focus in 1999.

Dec 1, 2017

This week, the Bowery Capital team hosted Aman Narang, President and Co-Founder at Toast, to discuss “Hybrid Selling Models: Building Successful Hardware & Software Sales Efforts.” Toast is a mobile point-of-sale application for restaurants, cafes, bars, clubs, and other businesses in the food service and hospitality space. Toast provides a comprehensive, fully-featured business management solution. As Aman is a Co-Founder at Toast, he built out the early sales machine at the business. We first dug in around the mixture of hardware versus software and how you specifically think about what you are going to lead with. Aman gave the listeners some great understanding about iOS versus Android from both the hardware and software side and how they thought about the form factor and custom hardware and software when launching Toast. Aman then discussed product pricing and considerations around hardware versus software. We close on this component of the discussion by talking through selling models and how a founder should consider local selling of their hardware and software with either an inside or outside sales model. Aman talked a lot about the specific profiles of people that he hired early on: ex-software sales people (obvious) or ex-restauranteurs (non-obvious). He spoke about competing with legacy vendors and how to win when thinking about the hardware or the software as the primary drivers. In the hospitality space, there is one glaring 800 pound gorilla in Micros Systems. Aman and I spoke about how they really built out a different market segment and really focused on a “harder” to win customer that Micros Systems was not even really competing in. He talked a lot about product pricing at scale and where they stand today on the blend of hardware and software pricing. Aman wrapped up the podcast with some high level thinking and tips and tricks that they learned in the first few years of business life. Aman Narang is President and co-founder of Toast. Prior to Toast, he worked on innovation initiatives at Endeca, now Oracle. Aman spearheaded the development of Endeca’s business intelligence platform as well as their mobile commerce platform, each of which became major business units. He holds BS and MS degrees in Computer Science from MIT and currently leads innovation and business development initiatives at Toast.

Nov 17, 2017

This week, the Bowery Capital team hosted Loren Alhadeff, Senior Vice President of North American Sales at DocuSign, to discuss "Pipeline, Pricing, Product, and Presentation." DocuSign is changing how business gets done by empowering more than 300,000 companies and 200 million users in 188 countries to sign, send, and manage documents anytime, anywhere, on any device, with confidence. During this week’s episode, Loren shares anecdotes and best practices from his almost ten years of sales experience across multiple stages of growth at DocuSign. We start our conversation by talking through early pipeline strategy and the mechanics of revising a strategy to meet the needs of a scaling business, from early-growth onwards. Loren walks us through how to think about top of the funnel efforts from year 1 to year 10, specifically mentioning the importance of tools in managing higher volume pipeline activity. Loren then shares his views on connectivity between sales and marketing and how that line of communication requires different degrees of attention (from both sides) throughout the evolution of a business. Second, we move on to a discussion around pricing. Loren walks through how to build an effective pricing roadmap, addressing tactics for maintaining a healthy balance between land grab (and the possibility of reducing price) vs. static pricing (and the risk of churning customers). From our seed stage perspective at Bowery, early pricing is mainly a derivative of a lean product that is still being built out, and a prudent pricing strategy for v1 products must account for future price increases and negotiations. Loren offers ways to manage through a fluid pricing strategy in a company’s early days. Particularly, he emphasizes the importance of cultivating an acute focus on communication between product and sales teams as a critical organizational framework for effective dialogue between these two functions as the business navigates more complex hypergrowth phases. Next, we cover a fundamental startup question “what drives decision making: product or sales and marketing?” Loren illuminates again on the requisite symbiosis between the two functions and its significance in keeping inertia in the marketplace. We conclude our conversation by zooming out and considering the broader stakeholders at play throughout a company’s growth. Specifically, Loren shares how to properly manage expectations across the management team and Board with regard to pipeline, pricing and product. Loren Alhadeff is the Senior Vice President of North American Sales at DocuSign. Loren joined the DocuSign team in 2008 bringing with him a breadth of executive sales leadership and operations experience. During his time at DocuSign, Loren has designed and built the company’s direct sales team. He is widely credited for growing the sales organization into one of the most respected teams in the industry today. Loren brings almost ten years of perspective from his time at DocuSign to the Podcast, and we are excited to get pick his brain on "Pipeline, Pricing, Product, and Presentation."

Nov 15, 2017

This week, the Bowery Capital team hosted Amy McIlwain, Global Industry Principal for the Financial Services vertical at Hootsuite, to discuss "Growing An Industry Vertical." Hootsuite is a platform that helps enterprises and brands manage their presence on social media. They are the most widely used social media management platform, used by over 16 million people around the globe and trusted by more than 800+ companies of the Fortune 1000.We focused the discussion on “Growing An Industry Vertical” from the sales standpoint of a software company. Amy joined Hootsuite two years ago having founded a consulting business in the financial services space and has great experience in the space. Hootsuite valued her expertise, connections, and approach. Therefore, they hired her to set up their first industry vertical: financial services. Growing an industry vertical is no easy task and Amy walked the listeners through the three phases of how to do this. We first talked about why a software company would think about a more vertical approach to sales, marketing, and customer success and how any founder should cover the analysis involved in determining whether to do this or not. Amy had a great system that she used in Excel to help Hootsuite understand the impact and thinking on the financial services vertical. Second, we ran through the set up of the financial services vertical and how the organization functions from a people, process, and systems standpoint. Amy and I talked a lot about growing an industry vertical from the standpoint of changing your sales materials, using marketing to drive your success (events, conferences, blog, case studies), and finally, how to think about the product and engineering changes as you grow out the vertical. Third, we talked about metrics for success - what has worked at Hootsuite, and the major lessons learned when thinking about growing an industry vertical. This was a very informative conversation, given Amy’s expertise. Amy McIlwain is Global Industry Principal at Hootsuite, the world’s largest social relationship management company with over 13 million users worldwide. She has appeared on FOX, CBS, ABC, and NBC as a social media expert, and delivers keynote presentations to financial service organizations around the world. With over 15 years experience in digital marketing and as founder of Financial Social Media, Amy’s presentations draw on her immense experience helping Fortune 500 banks, financial and insurance companies, operationalize social media to drive revenue, decrease expenses, and manage risk. She is a regular contributor to InvestmentNews, The Wall Street Journal Online, ThinkAdvisor, and in 2014 she was named by LifeHealthPro as one of the 24 Most Creative People in Insurance. In addition, her book, The Social Advisor: Social Media Secrets of the Financial Industry, has been featured as a best-seller on Amazon.

Nov 9, 2017

This week, the Bowery Capital team hosted Bill Siegel, CFO at SecurityScorecard, to discuss “Sales Pipeline Hygiene and Best Practices.” SecurityScorecard is a SaaS platform for cybersecurity ratings and continuous risk monitoring for vendor risk management. The company has raised over $60MM in venture capital, including its most recent round, a $27.5MM in Series C led by Nokia Growth Partners. With well over 100 employees, SecurityScorecard has been dramatically ramping its sales and other customer-facing teams. In this show, Bill walks us through his philosophy on the importance of sales pipeline hygiene, and why it’s potentially the most important step in building a predictable SaaS sales engine at the early stage. Today’s episode was recorded live at the 2017 Bowery Capital CFO Summit, where we had the pleasure of hosting Bill on a similarly themed panel: “Setting Actionable KPIs at Different Stages.” Pipeline is one of the most frequently underrated measures of sales health in pre-Series A enterprise SaaS companies. While bookings targets dominate founder thinking off the bat, understanding sales success or failure when it happens is almost more important. For example, a team might hit numbers in its first few months of sales. Everyone is happy and no one questions it: customers want the product and our sales team is killing it. Then, two months of bookings misses. What happened? Because no framework for understanding the sales process was instituted, the founders and the board are in the dark. To avoid these situations, startups—especially in enterprise SaaS—must build a culture of meticulous pipeline tracking and data collection; sales pipeline hygiene, in other words. A Seed stage founder might protest: we’re only a few people and don’t have sales ops resources! We just started to build pipeline! Complex sales metrics are for post product-fit companies! These are easy assumptions to make but they are all misguided. The key to successful early-stage sales pipeline hygiene—and seed-stage sales ops in general—is to keep the funnel simple enough to measure thoroughly. Limit the number of steps in your funnel, make sure each is tied to a specific milestone in the sales process, and ensure your entire team is on the same page regarding these definitions. Bill outlines one way a founder might structure her early “simplified” sales funnel. I’ll walk through them briefly below, as well as the sales milestone tied to each. Stage 1 -- Lead: To move an account to this stage, something has happened warranting moving a prospect—which is no more than a name, company, email in your CRM—into something that salespeople can work on. This may be inbound (whitepaper read, form filled) or outbound (SDR touch). Once the account is here, it is “actionable” and there is a next step that your team will take to begin moving it further into the sales funnel. Stage 2 -- Qualified: To move an account to this stage, your team must first “qualify” it. There are many sales frameworks that determine which boxes must be checked for qualification. Bill and I use BANT as an example, which calls for sales reps to verify Budget, Authority, Need, and Timing. We’ve discussed this framework and many others in past podcasts. Qualification usually occurs through sales calls, but can also occur over email, or sometimes via other methods of data collection like forms, webinars, or live events. Stage 3 -- Demo: To move an account to this stage, there needs to be proof that the dialog has moved into “active” selling mode. In the example Bill gives, that proof comes in the form of a successful demo, or an agreement to see one. At this point, your account becomes an “opportunity,” and part of your formal pipeline, both company-wide and on an individual rep basis. Stage 4 -- Proof of Concept (POC): To move an account to this stage, stakeholders have agreed to use your product as a precursor to a full purchase and contract. We’ve discussed best practices in POCs (and related SLAs) in past podcasts. But the key to successful POCs is the mutual commitment of resources, dedication to a limited timeline, and good faith agreement that should you “hit your marks” to the company’s satisfaction, a proper contract will be presented and signed. Bill suggests that over the course of a good POC, pricing should be discussed so that by the end of the process, negotiations are more focused on breadth of usage than negotiations on ACV. To successfully move an account beyond this stage, it must be signed and fully Closed / Won. With a simplified sales funnel like the above, your team can commit to thoroughly recording each of these steps in your CRM. This yields two critical tools: (1) an honest view of pipeline, and (2) a sense for conversion through the funnel, which helps one identify “leaks in the bucket” later on. In today’s episode, Bill also walks us through other keys to early sales pipeline hygiene. One, for example, is pipeline aging. Over time, a company will learn how long an account can stay in one stage before its age indicates that it’s no longer a valid opportunity. As reps are often incentivized to ensure their pipelines are full, it’s key for managers to keep an eye on aging to ensure deal freshness and mitigate “pipeline drift.” Later on, it’s possible to run more complex cohort analyses to get an understanding on aging’s affect on your sales process, but you can start simple: Bill suggests simply picking a date after which an opportunity must expire. Armed with a proper measure of pipeline, you can use it as a leading indicator for bookings, our original goal. Pipeline coverage is the easiest way to think about this early on. As Bill points out, it is hard to know what the “proper” coverage level is until at least a year or so post-product-market fit, in large part because enterprise sales cycles are different for every product and there’s often a lot of variance early on. But, you can still get a sense for what’s healthy and what’s not based on your initial win rates. In general, it’s hard to make an argument that you’re in a strong position to hit next quarter’s bookings if your pipeline coverage is under 2x targets. It’s important to remember that none of these measures are going to be perfect leading indicators early on. But by committing to a consistent process and sticking with it, you begin to generate historical data. Only then can your accuracy and forecasting ability can begin to improve. This is why, as Bill explains, sales pipeline hygiene should be a priority from day one. Bill Siegel is the CFO of SecurityScorecard, a role he has held for just over a year. Prior to SecurityScorecard, Bill served as Head of Private Market at NASDAQ. He landed in that role following NASDAQ’s late-2015 acquisition of SecondMarket, where Bill had been CEO. He originally joined SecondMarket as VP of Operations in 2011, prior to which he was SVP & Head of Corporate Finance at The Receivables Exchange. As a financially minded executive who has served in both the CFO and CEO roles, Bill is a perfect guest to speak on today's podcast topic. Happy listening!

Nov 6, 2017

This week, the Bowery Capital team hosted Oliver “OJ” Jay, Head of Global Sales at Asana, to discuss “Sales Model Evolution From Freemium To Enterprise.” For those who don’t remember, we had our old friend OJ on the Podcast to talk about selling SaaS overseas when he was at Dropbox. Today, OJ runs the Global Sales organization at Asana. Asana provides an application that makes it easier for teams to track their work with greater clarity, accountability, and efficiency. During the Podcast, we had a unique conversation about lessons learned from major SaaS companies growing from freemium up to small and medium sized deals and then to large enterprise deals. First, we ran through the movement from free to freemium and how to think about what matters when making this decision at your own company. Usually these are organizations with a ton of free users and so coming up with an informed decision on when to move into freemium is super important. OJ talked a lot about his experience at Dropbox and now at Asana thinking about how they made the decision as well as product, pricing, competition, and other elements to move from free to freemium. OJ even spoke about how to set up your revenue organization correctly in a freemium business. Second, we walked through how a business should think about moving from freemium up to larger deal sizes which we call SMB for the purposes of this Podcast. OJ runs through an exercise that he did at Dropbox called density mapping and how organizations should use this to make product decisions around moving upmarket. We close on this segment talking about the CAC / LTV ratios of sales organizations and when to move further upmarket into what is commonly known as the enterprise segment. Third, we walk through probably the trickiest stage which is thinking about the option to launch into the enterprise segment (F2000 in our example). This segment is a different muscle altogether and OJ walked us through how to really change and build your organization to get this right. He sees most founders fail here and talked a lot about the main lessons learned over many years. We closed the Podcast with some points of view on who has done well moving from freemium to enterprise: Zendesk, LinkedIn, New Relic, and Box were some that OJ named. On the downside, we talked about Evernote and the danger of giving up too much value up front. All in, it was a great Podcast chock full of information and thinking, so give it a listen! Oliver Jay is the Head of Global Sales at Asana. Prior to Asana, he scaled the Dropbox sales team from 20 to 100 people and across multiple geographies. Previously, Oliver worked at Morgan Stanley and New Enterprise Associates (NEA) where he invested and worked alongside entrepreneurs in consumer internet, cleantech and enterprise SaaS companies. Oliver earned his B.A. from the University of Pennsylvania and his MBA from Harvard Business School.

Nov 3, 2017

This week, the Bowery Capital team hosted Bill Macaitis, a former marketing executive from Slack, Zendesk, Salesforce and many more, who continues to advise the world’s fastest growing SaaS companies today. On the podcast we discuss “Finding The Right Marketing Metrics For Your Team,” drawing from the best practices that Bill applied to his extremely successful teams through many stages of growth. In a marketing world full of more acronyms than the human mind can grasp, and the rise of specialized functions like demand generation and account-based marketing, how do we hone in on proper measurement? In today’s episode, Bill breaks it down for us from A to Z, and “beginner” to expert” level metrics and methods to get your marketing team on the right track. Deciding what to measure is one thing, but actually capturing the information is another challenge. With this in mind, Bill also takes some time to share his favorite methods with us for capturing data, from NPS and CSAT surveys to in-product analytics and more. Whether you’re brand new to marketing, or a seasoned veteran looking for inspiration, Bill’s advice on how to get your marketing measurement strategy kickstarted is invigorating, fun, and informative. Bill has a passion for how to scale and structure go-to-market at SaaS companies to achieve hyper-growth with a unique customer centric approach. He spends his day-to-day working with CEOs to design, recruit, interview and build out world class marketing and GTM organizations, and has successfully done so for the likes of Slack, Zendesk, Salesforce and more in recent memory. As an energetic Star Trek and startup fan alike, he’s all about planning for the future, and executing on its foundation today.

Oct 16, 2017

This week, the Bowery Capital team hosted Wade Foster, the Founder and CEO of Zapier, to discuss "Optimizing Your Partnerships." Zapier helps automate the integration of your favorite apps to share data between them, and bring them together. With an app directory of 750+ companies, including Salesforce, Slack, Dropbox, Gmail, and more, Zapier has created a strong network that has become essential to companies big and small that are trying to get the most out of their cohesive tech and tools stacks. Zapier's current customers include industry leaders like Buzzfeed, Spotify, InVision, Adobe, and the company is growing extremely fast. In today’s episode, Wade walks us through the unnecessary ways companies make partnerships hard to accomplish, and some simple strategies to start to build your own network. He explains effective methods for establishing strong partnerships, how to avoid ones that will distract your company, and the ways you can measure success. With the user always in mind, Wade and the rest of the Zapier team are laser-focused on engaging in partnerships for the sake of building relationships that ultimately benefit the end user. Throughout our discussion, he guides us on how to go about tackling this kind of approachWade is passionate about entrepreneurship and startups, and as the founder of Zapier, he has spent the past six years finding ways to make life easier for the users trying to connect today’s favorite apps. Prior to founding Zapier out of Y Combinator, Wade worked as a leader and manager in email marketing and customer development for a variety of transforming businesses. Wade attended the University of Missouri, where he received a BS in industrial engineering and also received his MBA.

Oct 12, 2017

This week, the Bowery Capital team hosted Ray Carroll, VP of Sales at Engagio to discuss “Developing Culture and Brand at an Early Stage." Engagio is a software company that helps B2B marketers drive new business, expand relationships with high-value accounts, and scale their Account Based Marketing programs. Engagio provides data and operations for an account-centric foundation, analytics, and insights to measure engagement, and an orchestration platform to execute integrated ABM plays that drive revenue at every stage of the customer journey. In today's episode, Ray and I discuss the importance of defining and developing the culture within your organization and a recognizable and respected brand outside of your organization. We begin by discussing why culture and brand should be top of mind for executives in the early days. We then move into how exactly you should think about your culture and who should be in the room as you try to define it. Ray then discusses how you maintain that culture as your team rapidly grows. Ultimately, the conversation shifts to talk about your external brand. We go over the many reasons it is critical to define your brand externally as early as you can. These reasons include everything from boosting your ability to recruit top talent, to shortening your sales cycles because the customer you are pitching has already heard of and respects your brand. We had a great discussion and the chat was action-packed. Ray currently leads all early stage revenue activities at Engagio. Prior to Engagio, Ray spent 7 years at Marketo where he was employee #28 and the 3rd sales hire in the door. Ray helped build framework for the SMB sales organization as a VP, Director, Manager and Individual Contributor. Ray was pivotal in helping grow Marketo from 1M to 10M to 100M+ in ARR. Prior to Marketo, Ray was the 3rd sales hire at Genius.com, a VC-backed SaaS startup that was later acquired by Callidus Software. 

Oct 5, 2017

This week, the Bowery Capital team hosted Dannie Herzberg, Head of North American SMB Sales at Slack to discuss "Moving Upstream: How to Build a Sales Org in Freemium SaaS." Slack is a team communication application that provides services that include real-time messaging, archiving, and search for modern teams. It offers one-on-one messaging, private groups, ongoing chat rooms and direct messaging, as well as group chats organized by topic. Slack was established in 2013 and went on to be one of the fastest startups to hit the "unicorn" landmark. In today's episode, Dannie and I discussed the ever important topic of moving upstream as a SaaS company. We touch on the relatively new business model of freemium and how it has impacted the SaaS industry today. We first cover companies that are able to build large networks of users and how to think about when is the right time for your organization to build a sales team on top of these free or freemium users. Dannie then gives the audience some great ideas and insights into how Slack thought about this early on and the lessons learned since her time at the company. Third, we talk a lot about the segmentation that Slack uses to determine when someone should move from freemium to her team and cover ideas like “progressive profiling” and other unique insights. Next, we cover the sales process map for Slack and how the demo stage of freemium companies differs greatly from a traditional sales process. We then dive into some of the product features and gating factors that Slack employs in their company. Finally, we close on some of the ideas around metrics, tracking, and the interaction between the marketing, sales, and customer success teams. We had a great discussion and the chat was action packed. 

Sep 28, 2017

In today’s episode, Meghan begins by defining an internal growth ladder and emphasizes the importance of being able to promote from within as your company scales. She explains that as a manager, it’s your responsibility to develop your team to make them successful in their next role. She notes that checking in with your reps about their career goals in 1-1s creates consistency and that it is never too early to start thinking about building a ladder. She mentions the concept of building in mini-promotions or tiers for your team by adding title bumps such as “senior” to roles to show growth. She also explains that growth doesn’t always have to be vertical and that reps should be able to grow laterally into different parts of the organization such as Customer Success or Marketing if that’s what they become passionate about. She then dives into how she determines when a rep is ready for a promotion and explains how Zendesk has created a methodical approach to career pathing, by outlining a concrete “Career Template” and SWOT analysis that reps fill out and go over with their manager. We end the podcast by talking about pitfalls or red flags that early founders or managers should be cautious of as they hire and begin to build internal growth ladders for their teams. Meghan LaTorre is passionate about building teams, mentoring future sales stars, and streamlining processes. She is currently the Manager of Velocity Sales (North America) at Zendesk, a company that builds software for better customer relationships and empowers organizations to improve customer engagement. Prior to that, she has over 10 years experience in SaaS revenue generation at some of the most notable companies in the industry, holding various sales roles at companies such as Salesforce, Facebook, and Betts Recruiting.

Sep 26, 2017

This week, the Bowery Capital team hosted Morgane Palomares, Marketing Manager, East Coast at Github, to discuss "Industry Marketing Programs and How to Build Them at Every Stage.” GitHub is how people build software. With a community of more than 24 million people, developers can discover, use, and contribute to over 67+ million projects using a powerful collaborative development workflow. Whether using GitHub.com or your own instance of GitHub Enterprise, you can integrate GitHub with third party tools, from project management to continuous deployment, to build software in the way that works best for you. Morgane begins the show by defining industry marketing programs as taking your horizontal audience and slicing it vertically so that everything you’re doing from a marketing perspective is vertically specific to a certain buyer. Next, she dives into when companies should begin to think about building industry marketing programs. Morgane explains that every company where she has built these programs out, has been at a very different stage of their growth, and that it ultimately depends on the capabilities of the sales team and needs of current and future customers. To that end, she discusses how earlier stage companies should focus on prioritizing their top industries while larger companies can deploy multiple resources and robust teams to focus on various sectors. Next, we chat about the time and resources that a company should plan to deploy when creating industry marketing programs and the steps necessary to making sure that the program is set up properly. One of the key things that she recommends is making sure that sales is completely aligned with the idea of segmenting by industry and notes that this is typically most successful when companies are already on a territory based system. We end with a few tactical takeaways for our listeners where she mentions her top 3 tips and tricks for making sure that your industry marketing program is set up for success.

Sep 7, 2017

This week, the Bowery Capital team hosted Omar Divina, VP of Sales and Customer Success at HyperScience, to discuss "How To Differentiate Your Product When Selling Into A Crowded Space." HyperScience is an artificial intelligence company specializing in the automation of office work for Global 2000 companies and government organizations. Their machine learning software takes over menial work that people are doing today and frees employees to focus on more complex tasks. In today’s episode, Omar starts off by walking us through the importance of cutting through the noise in a crowded space. He explains that the best way to learn product market fit is to have as many prospect calls as possible to properly position the solution. He then explains that as the market becomes better educated, buyers focus more on use cases and the business pains that vendors can solve. He notes that it’s imperative that companies remember to focus on what they are trying to solve with their business rather than getting too caught up in the technology. In a space like AI, it’s important to be able to articulate how the tool is utilizing AI and machine learning techniques to continue to explain the value. When it comes to marketing, Omar notes that in a space like enterprise AI with a broad spectrum of vendors, the impulse might be to cast a wide net. However, as the business continues to refine its goals and strategy, it’s important to market to the right decision makers within an organization. He also explains the importance of sales reps being able to say “no” as to allow the organization to align around a core set of products. As the session closes, Omar walks us through the need to make sure that all parts of the business are aligned with the services needed by customers and the importance of Customer Success being involved in the sales process, even before the deal is closed to ensure consistency and alignment going into deployment.

Aug 17, 2017

This week, the Bowery Capital team hosted Trenton Truitt, SVP of Worldwide Sales and Customer Success at Wizeline to discuss “Coaching Your Employees Through Their Career Path." Wizeline transforms how teams build technology. Its customers accelerate the delivery of innovative products with proven solutions, which combine Wizeline’s intelligent product strategy and road mapping software with full-stack, agile development services. With decades of experience building disruptive technology in the heart of Silicon Valley, Wizeline’s team shares a proven track record of enabling companies to achieve breakthrough results with software and services. Customers of Wizeline include some of the fastest-growing software companies, as well as many of the world’s most established brands, including News Corp, Yahoo!, Sparkcentral, Nuance and many others. In today’s episode, Trenton joins us to discuss how to find, nurture, and value a mentor relationship. Trenton kicked off the topic by explaining why mentoring and coaching are important to him. He emphasized the need to engage mentors and follow through on their advice. He uses anecdotes from his own life and draws from past experiences with both mentors and mentees. He also talked about the differences of formal and informal mentoring. For Trenton, informal mentorships are key. This led to a more in-depth conversation on how Trenton mentors and coaches his own people. First, Trenton reviewed the process by which he coaches his employees and then discussed how he operationalizes that experience. He also described that many of his meetings with mentors are informal ranging from lunches to one-on-ones. As Trenton’s gains more mentors, he described how he thinks through allocating time to each individual and how he adjusts his style depending on the person. With that, he provided a few examples that allow listeners to visualize the process. Next, Trenton mentioned the importance of holding mentees accountable to their metrics and goals. As the program continued, Trenton described how he provides curbside coaching and keeps his team on track to reach goals. He also touched on how mentoring and formal training for salespeople tie together and how this was set up at Wizeline. To close out the session, Trenton discussed training and tools to help coach teams.

Aug 10, 2017

In today's episode, we host Promise Phelon, CEO of TapInfluence, to discuss "Transitioning From Services To SaaS." TapInfluence was founded in 2009 with a singular purpose – to facilitate real conversations between people and brands by tapping into the power of digital influencers and their authentic, trusted content – allowing consumers, influencers, and brands to get heard. Using TapInfluence’s leading-edge SaaS platform, marketers can automate the time-consuming process of identifying and engaging with relevant digital influencers, as well as collaborating with them to create compelling content that motivates consumers to take action. TapInfluence’s customers include a who’s who of leading brands, such as Kraft, Horizon Organics and P&G, and agencies such as Golin, RhythmOne and Ignite Social Media. Through Instagram, Facebook, Pinterest, Twitter, YouTube, Vine and blogs, TapInfluence reaches over 1 billion consumers. In today's episode, Promise joins us to discuss transitioning from services to SaaS. She starts by explaining that TapInfluence initially started as an agency that underwent a transition to become the software company they are today. Promise touches on the challenges faced during this type of transition and explains the four different phases she and the business went through. She talks about how to deal with the difficult task of telling happy customers your business is changing and how to keep these customers. Retrospectively, she says she would have waited a little longer to scale TapInfluence after its pivot and she gives us a few trends to look at that may help indicate when the time is right to scale. Promise talks about how to identify power users in a newly-pivoted software business and explains the important role that product and customer success teams play during this period. She talks about the customer advisory boards that TapInfluence created and urges listeners who create these types of boards to make sure they include prospective customers, along with current ones. She says having board members who challenge certain decisions, serve as a sounding board and give honest feedback are key. Finally, Promise wrapped up by saying speed and having board and investor alignment is crucial during a transition from services to SaaS.

Jul 21, 2017

In today’s episode, we host Conner Burt, COO of Lessonly, to discuss "Beyond Individual Contribution: Learning As A Sales Team," how sales teams can go beyond working day to day as individuals, and learn together as teams. Lessonly is modern team learning software used by over 650,000 learners at more than 350 companies to translate important work knowledge into Lessons that accelerate productivity. Sales teams across the world use Lessonly to reinforce best practices, accelerate rep performance, and close more deals. Support teams across the world use Lessonly to serve customers faster, drive consistent support, and elevate the customer experience. Lessonly empowers teams like those at Stripe, Birchbox, Modcloth, FiscalNote, Thumbtack and more to learn better day in and day out through their lesson building software, which makes Conner an expert on today’s topic. As we all know, sales is fiercely competitive and not just between competing companies. Often times the best reps will hoard their knowledge or simply keep it to themselves unless the culture around them supports and prompts learning together. As both a student and teacher of sales and learning cultures, Conner shares with us some ideas on how teams can break this conundrum and proactively and constructively learn together to sell better. This podcast is packed with tactical ideas and step by step suggestions here. Remember, the whole (of a sales team) is always greater than the sum of its individual (seller) parts.

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