Setting Sail from Sailthru

Inevitably, there are moments in our lives that we recall down to a very specific detail; for me, one of the most momentous of those occasions was penning my business school admission essay in the throes of the economic crisis in October 2008. In that essay I asserted that “…I am confident that venture capital is going to be a great next step in my story, and that my ultimate destiny is indeed to run my own internet company.”

It turns out that my passion for operating companies meant that venture capital was not actually the great next step in my journey at that time, but I share this anecdote as context for the significant professional update I’m announcing today: after nearly seven amazing years with Sailthru (this last one managing several other great brands across our parent company CM Group), I will be transitioning away from the business at the end of the year to assume a partnership at Primary Venture Partners here in New York (…so 11 years later, the dream is indeed alive!).

My decision to leave Sailthru has hands-down been one of the most emotional and difficult exercises I have ever navigated. Watching our business grow from 50 people at Sailthru Varick Street to nearly 700 people across six global brands has been the ride of a lifetime. The journey that our team endured through the ups and downs that come with any growing business was a very real one, and one that I will carry with me for the rest of my career: our first million-dollar deal and all those that followed, our first placement on the Magic Quadrant, a 55-point improvement in NPS that put us far ahead of technology benchmarks, a successful exit, I could go on.

While I held executive titles in prior roles, I truly grew up as an executive at Sailthru, and for that reason it will always hold a special place in my heart. That said, I am a firm believer that the best time to make a transition is when your business is in a position of strength, and here we are: we have found an amazing new home for Sailthru with the CM Group acquisition, our operating metrics are the strongest they’ve ever been, we are on our fastest hiring clip yet, and we are aggressively investing in accelerating Sailthru’s growth. My VP team is thriving on their own, and is well-suited to lead us through the next stage of our journey.

As I reflected on what I wanted to do next, I had a very significant personal revelation: when I embark on my next executive adventure, I want it to be in the capacity of running my own company. That said, an exciting next chapter awaits in the meantime. Incidentally, at Primary’s annual summit this fall I had the opportunity to hear from Jill Ellis, former coach of the US women’s national soccer team, who offered an interesting perspective on why she is such a phenomenal coach: because she was a “student of the game” while growing up in the UK and limited in her ability to play the sport. I am beyond excited to be a student of the game as an operating partner at Primary, as I know the years ahead there will prime me to be an outstanding founder and CEO at some point down the line.

Primary is hardly a foreign place for me; I had the good fortune of meeting Brad Svrluga when he invested in Savored back in 2010, and he became an instant favorite once we got knee-deep on cohort analysis; our relationship has persisted over quarterly catch-ups on all things NY tech for years, and he will certainly go down in the books as one of the most effective salespeople I’ve ever come across, because the last time I was this excited about a professional endeavor was when I quit my banking job to join my first startup in 2006. I am also privileged to have gotten to know Brad’s co-founder Ben Sun over the past few years, as well as soon-to-be fellow operating partners Cat Hernandez and Bob Peruzzi; Cat and Bob’s impact on the Primary portfolio has been nothing short of tremendous, and I can’t wait to join them in supporting Primary’s outstanding companies. The broader Primary team is equally as impressive, and I am proud to be able to call them all my colleagues.

I could ramble on for days about why I am so bullish about this new opportunity, but I’ll spare everyone of the novel and offer a few quick highlights:

• Love of startups. This really says it all; I love spending time with passionate entrepreneurs and advising startups. During my time at Sailthru, it was always important to me to find time to volunteer with organizations such as Venture for America and Entrepreneurs Roundtable Accelerator. To be able to do this work as a full-time job is truly a dream come true.
• Opportunity for impact. I will forever be motivated by my ability to affect change and drive results, which is why I take such joy in working with customers — yes, it’s been fun to run a large organization at Sailthru and to have an impact that way, but it’s also been a lot of fun to coach hundreds of different customer organizations on their marketing programs! I am excited to partner with a new set of customers — Primary’s portfolio companies, most of whom chose to work with Primary on account of the firm’s hands-on model — to drive continuous improvement across their operations.
• New York tech ecosystem. When I authored the aforementioned b-school essay in 2008, I was convinced that I would move to SF after finishing my MBA and that I would never return. I never could have anticipated the proliferation of New York tech that the financial crisis would ultimately inspire. As a native of the tri-state area, I couldn’t be more pumped about it. As I explored a variety of possible post-Sailthru paths, I met with dozens of founders and CEOs here in the Big Apple, and I could not be more bullish on the road that lies ahead for us as a community. There are exciting companies all over the world, but boy am I excited to lean in with some fantastic ones in my backyard.
• SaaS and consumer split. Prior to my time at Sailthru, I spent several years leading growth for consumer businesses; in fact, one of the reasons I went to work at Sailthru was because it was a SaaS business that serviced those very same consumer companies. I love these spaces equally, and am excited to work in a role where I can flex both muscles.

As I look forward to this exciting new chapter at Primary, I owe a number of thanks: first and foremost, to my “personal board of advisers,” who supported me in my soul-searching — everyone from prior board members, CEOs, colleagues and mentors right through to my mom (on the receiving end of many hour-long phone calls) and my husband Mike, my self-proclaimed personal CEO (“Cassie Enablement Officer”). I owe particular due to Sailthru’s founders Ian White and Neil Capel; to our subsequent CEO Neil Lustig, who constantly pushed me at Sailthru and encouraged me to take our CRO role two years ago; and to CM Group’s CEO Wellford Dillard, who gave me the opportunity to lead an exponentially larger organization, and by extension paved the way for many talented individuals at Sailthru to further their careers. I am beyond privileged to have worked with you all.

I regularly tell our team that, “if we do everything in our power to make our customers wildly successful, we’d have to catastrophically f*ck something up to not succeed as a business” (pardon my French). So last but certainly not least, I owe a debt of gratitude to the amazing colleagues, customers and partners who made my Sailthru journey what it was: our customers and partners for making our jobs fun and exciting, and to Team Sailthru for making the magic happen. When I was running for student council in middle school, my dad encouraged me to run on the platform of “Team Cassie” and stressed that great leaders are only as strong as the teams that support them; my years at Sailthru crystallized that much for me. Thank you ALL for your tremendous support; it’s been an incredible sail!