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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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Bowery Capital Startup Sales Podcast
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Now displaying: 2017
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.

Jul 13, 2017

This week, the Bowery Capital team hosted David Aronica, Business Development Manager at Splash to discuss “Hiring Your First BDR." Splash is an event marketing platform that enables users to create event experiences. The end-to-end Splash platform empowers users to create memorable event experiences through beautiful design, powerful planning and analysis tools, and meaningful integration of email marketing and social media. Splash enables brands like Facebook, Spotify, Salesforce and Anheuser-Busch to attract more of the right people, easily scale out their process and workflow, and capture the 1000's of data points every live event throws off, to inform future events and rest of your marketing mix. In today’s episode, David joins us to discuss hiring your first BDR. He initiated the conversation by providing his opinion on whether managers should spend more time training or hiring new BDR's. In the past, he's spent time hiring too many new BDR's, which led to layoffs due to the fact he didn’t have the time to train them and invest in his team. David discusses hiring veteran versus younger, millennial BDR's and what he sees as the ideal business development representative candidate. Initially, he hired veteran BDR's that he thought could fall in love with the product and wanted to move up quickly in the organization. He allows these more senior BDR's to see the metrics and parameters upon which they are ranked on per month. David goes on to discuss hiring millennial BDR's and the keys to managing them. David looks for solution-oriented, tenacious personalities that are coachable in these younger hires and he makes it his goal to embrace all individual learning styles as a manager. When it comes to both veteran and millennial BDR's, David believes that being completely transparent about expectations leads to relationships where new hires trust him and understand why he does what he does. He touches on the mistakes he's made in scaling out his teams in the past, among them: not training ramped up reps, not providing clarity around what it takes to get promoted, and only looking at numbers instead of investigating the deeper issue. David’s final thoughts on hiring your first BDR are to invest in them, since they are the future of your organization.

Jun 29, 2017

This week, the Bowery Capital team hosted Evan Bartlett, Head of Inside Sales at ZocDoc to discuss “Hiring Your First Sales Representative." ZocDoc is an online medical care scheduling service, for end users integrating information about medical practices and doctors' individual schedules in a central location. Each month, millions of patients use ZocDoc to find in-network neighborhood doctors, instantly book appointments online, see what other real patients have to say, get reminders for upcoming appointments and preventive checkups, fill out their paperwork online, and more. With a mission to give power to the patient, ZocDoc’s online marketplace delivers the accessible and simple experience patients expect and deserve. ZocDoc is free for patients and available across the United States via ZocDoc.com In today’s episode, Evan joins us to discuss hiring your first sales representative. The conversation started by discussing when to hire the first sales representative. This included the process of building a sales process and its link to the go-to-market strategy. Next Evan discussed when to identify the market and key factors in this process. Evan then summarized the details around the background and skillsets of a sales representative. Evan discussed his thoughts around the structure of the hiring process and the onboarding and ramp up process for new sales representatives. Next Evan discussed setting benchmarks for the first hire and tying those metrics to compensation. In this hiring process, Evan discussed how he made several mistakes and how he pushed ahead. We then transitioned to expanding the sales team from 1 to 100. Evan discussed how to maintain culture despite high growth. Next Evan described how the hiring process shifts with a larger team and how these sales representatives differ from the original team. Evan then discussed the importance of repeatable sales to the business and how he thinks about that skill in hiring new sales representatives. Evan closed out the session by providing his go-to tactics and tricks in the hiring process.

Jun 22, 2017

This week, the Bowery Capital team hosted Jason Dorfman, Inside Sales Manager at Rubrik, to discuss "Sales Recruiting 101 for Founders." Founded in 2014, Rubrik offers live data access for recovery and application development by fusing enterprise data management with web-scale IT, and eliminating backup software. This marks the end of a decade-long innovation drought in backup and recovery, the backbone of IT. Within minutes, businesses can manage the explosion of data across private and public clouds. Rubrik is trusted by some of the world's leading companies, including Driscoll's, JLL, the Tampa Bay Rays and Berkeley College. In today's episode, Jason joins us to discuss sales recruiting 101 for founders. He starts by touching on the importance of building your product and getting market validation before hiring your sales team. He discusses how to think about hiring your first salesperson and whether it should be a lead generating SDR or an inside sales rep with closing experience.He talks about how what he pitches candidates on has shifted as the company has grown from startup to 400+ employees and how his interview style has changed with that growth. Jason tells us his favorite question to ask during the interview process and recommends using recruiters as a resource to fill pipeline. He says he allocates about 30% of his time to recruiting and finds it to be seasonal - spending a lot of his time in interviews and on phone screens. For Jason, when it comes to hiring, the most important thing is finding the right people. He even urges managers to be willing to fall short of hiring goals if you haven't found the right people during an interview process. He says every time you hire a salesperson, you should believe there is a chance they can be the number 1 salesperson at your company. Finally, Jason advises anyone who is hiring to be patient, keep a cool head and think long term - even if you are under intense pressure to fill roles - and he leaves us with a great quote: "good people fix bad process, good process and bad people is not a good situation."

Jun 15, 2017

This week, the Bowery Capital team hosted Bobby Long, VP of Sales at Dedrone, to discuss "Insight Selling In The Modern Market." Dedrone is the first automated drone security platform; an extension of physical and cyber security into the airspace that protects a vulnerability gap exploited by the advances in consumer and commercial drone technology. Their most notable references include the Clinton-Trump presidential debates, the Suffolk County prison in New York, the Royal Family of Qatar, Citi Field (the New York Mets' stadium), and the World Economic Forum in Davos. In today's episode, Bobby joins us in the studio to discuss insight selling in the modern market and why he takes this approach. First, he talks about the differences between solution selling and insight selling. He defines solution selling as "Sales 101" where you get a deal by finding customer pain points and fitting your solution to those pain points within your prospect's budget. Bobby sees most companies using solution selling and sees an opportunity to differentiate by using insight selling, which he says allows you to position yourself as a subject matter expert and establish credibility and legitimacy. Bobby says that if you employ insight selling the right way, you form more of a partnership with your prospect or customer, leading to a higher rate of renewals. He discusses the challenges of insight selling and why it's not for every rep, along with some of the difficulties he's faced teaching reps how to insight sell and some solutions for getting around them. Finally, Bobby says not to be afraid of making visionary statements during the sales cycle versus just talking about what your product does, and he recommends reading this Harvard Business Review article.

Jun 8, 2017
This week, the Bowery Capital team hosted Jen Grant, Chief Marketing Officer at Looker, to discuss “Marketing Stack Essentials.” Founded in 2011, Looker is a business intelligence software and big data analytics platform that helps you explore, analyze, and share real-time business analytics easily. Approaching the Business Intelligence industry in a new way, Looker believes that businesses can only thrive when information is easily accessible and consistently defined across the entire organization. Looker’s customers include industry leaders like Kohler, Nordstrom, Lyft, Athena Health, and Spotify, amongst others. In today’s episode, Jen joins us in the studio to discuss everything from her early brief career as an actress with voiceover skills (no pressure on us!) to building marketing tool stacks that work well now, and scale smoothly later. Jen challenges us to think about where we put our precious marketing budget, and who owns those tools within your organization so that you’re actually getting your money’s worth. A critical part of the discussion was digging in on the variety of places you can go to learn about your tools – from Facebook Groups to G2 Crowd, and the order in which you should be implementing your stack. Finally, we finished up by asking Jen if she had only one marketing tool to use for the rest of time what would it be and she gave us sound advice here without hesitation. Tune in to find out which one tool she would use and hear more from Jen Grant!
Jun 2, 2017

This week, the Bowery Capital team hosted Grant Halloran, CMO at Anaplan, to discuss "Analyst Relation Strategies That Work." Anaplan is driving a new age of connected planning. Large and fast-growing organizations use Anaplan’s cloud platform in every business function to make better-informed plans and decisions and drive faster, more effective planning processes. Anaplan also provides support, training, and planning transformation advisory services. In our episode today, Grant joins the podcast to discuss analyst relation strategies that work. First, he talks about how the landscape over the last 10 years has shifted from working strictly with Gartner and Forrester to working with newer, independent analysts that produce their own research and blogs, as these smaller guys can be very important to companies serving niche type markets, while continuing to work with the two giants. He says to nail analyst relations, you must start by engaging analysts very early on. He stresses the importance of a CEO or founder working with analysts, as they want to hear why you've decided to enter the market you have, and not to think of analyst relations as a marketing function for a CMO or Head of Sales to figure out. He's helped companies become Gartner Magic Quadrant leaders and touches on ways to help your company get there, including the need to become a paying customer. He gives pointers if you get to a point where you feel you've invested in analyst relations and aren't seeing any traction in write-ups or reports. Grant says that your pitch to an analyst is a level above a normal sales pitch, and that running your sales pitch by an analyst for feedback and to see how you differentiate from competition is a good idea. He talks about quantifying and measuring success with the analyst community and explains how Anaplan does this. Grant wrapped up by urging CEO's to make analyst relations one of their top 3 or 4 priorities and saying that having a good attitude towards the community will resonate with analysts and help you in the long run.

May 26, 2017

This week, the Bowery Capital team hosted Brian Kelly, CEO at Kissmetrics, to discuss "Optimizing New Product Launches." Kissmetrics is a behavior analytics and engagement platform that was built to help marketers and product teams increase conversions, drive engagement and grow retention. Over 900 companies, like Unbounce, SendGrid, Outbrain, Lucid Software, and more use Kissmetrics to quickly identify and take action on roadblocks across their growth cycles. In our episode today, Brian joins the podcast to discuss ways for companies to optimize new product launches, something Kissmetrics recently did with their release of “Kissmetrics Campaign” and the rollout of their Customer Engagement Automation platform. He discusses how Kissmetrics goes from ideation stage to the actual release of a new feature or product, and explains that in this process he relies heavily on feedback from customers. Kissmetrics’ latest product launch was a big paradigm shift, from the analytics side to the engagement side, so he explains how first important it was to get internal buy in from team members. After getting buy in, The Company prioritized teaching team members as much as possible about the product, and held internal lunch and learns which included getting and giving demos and going through non formal certifications. Next, Brian focused on how to roll out the product externally. An early adoption beta program allowed Kissmetrics to have a constant feedback loop at the earliest possible stage and helped them optimize features, functionality and design of the product for users. When it was time to figure out pricing, Brian stressed the importance of making pricing models easy to understand as prospective clients can get fed up if pricing is too complex. Brian wrapped up by explaining that getting feedback from prospective users outside of your company on features and products is crucial.

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