Allison Pickens is the COO @ Gainsight, the company that provides everything you need to turn your customers into your biggest growth engine. To date Gainsight have raised over $184m from some of the world’s best VCs in the form of Lightspeed, Bessemer, Insight Venture Partners, Battery Ventures and Salesforce Ventures just to name a few. As for Allison, in her 5 years at Gainsight her list of achievements in endless from running all functions that drive value for Gainsight customers, now a 150 person team, to building out the corporate development function to being the right hand to the CEO. Allison is also an Entrepreneur-In-Residence at Bessemer Venture Partners and sits on the board of RainforestQA. Before Gainsight, Allison started her career in NYC with stints at Bain and The Boston Consulting Group. In Today’s Episode We Discuss: How Allison made her way into the world of SaaS with Gainsight from her start in finance at Bain in New York? What does a strategic plan really mean to Allison? What is included in it? How should it be structured? In terms of ambition, how does one set ambitious enough plans to be a stretch but not a stretch too far? How does one tie their strategic plan to their financial plan? What is the right way to communicate this throughout the organisation?    Why does Allison believe product marketing and customer success are the new sales and marketing? What have been Allison’s biggest lessons on how to effectively measure adoption? Who is accountable to this number? CS or product management? Does Allison believe that marketing needs to be held accountable to a number directly tied to revenue?  How does Allsion respond to the common negative of “services revenue”? What is an acceptable ratio of services to software revenue? How can one approach setting up a services team for scale? Why is having such a great CS team actually bad for product development in the long run? How can one mitigate this? Allison’s 60 Second SaaStr: What does Allison know now that she wishes she had known at the beginning of her time with Gainsight? How often should CS check in with their customers? What does that look like?  If on a tight budget, how should one staff a CS team? If you would like to find out more about the show and the guests presented, you can follow us on Twitter here: Jason Lemkin Harry Stebbings SaaStr Allison Picken