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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: November, 2017
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.

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