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Women in Enterprise: Cassie Young at Sailthru

This series features profiles of some of the top women leaders within our enterprise technology community here in NYC. We hope by highlighting the terrific work, stories, and career trajectories of these women at top venture-backed startups and operating roles will continue to encourage more women to consider careers in enterprise software.

As a follow up to our sold-out Navigate 2018: Women in Enterprise Tech Summit here at Work-Bench with Salesforce Ventures, we are continuing to recognize and amplify these impressive women in NYC enterprise tech.

Cassie Young is the Chief Commercial Officer at Sailthru.

What were you doing before this current role in enterprise tech, and how did you get to your current role?

I often joke that if someone had told me ten years ago that I would wind up working in B2B software, that I’d tell them they’d lost it — but alas, here I am! I made the transition just over five years ago, and came into enterprise tech through a different angle than most: I previously held the same seat that most of our (Sailthru) clients hold. More specifically, I ran performance marketing teams for several years prior to Sailthru, and was actually a Sailthru customer for two years before joining the team full-time. (It’s worth noting that I started my “tech” career covering media and technology companies on Wall Street, so I had spent a decade in tech sector, and my quantitative thirst runs deep.)

In my prior roles, I had spent a lot of time understanding buy vs. build decision frameworks and had exposure to hundreds of different vendors and partners. I liked what I saw in the team and the product at Sailthru (though it’s a running joke that I was a very noisy client!), and I spent a lot of time getting to know Neil Capel, Sailthru’s founder, while still on the customer side. Neil and I did an 18-month dance before I formally made the leap to the SaaS side and looking back, it’s been the single best move of my career. Ultimately, the idea of leaning in on marketing programs for 300+ different brands versus just one was very appealing and exciting to me; I do not think I would have wound up in enterprise tech had it not been at a company focused on marketing tech or data/analytics — you must always have passion for what you are selling!

I’ve had a pretty unique journey at Sailthru. I was initially hired in a bit of an amorphous role, with an operating objective to improve our marketing subject matter expertise and to build more data-driven and strategic customer teams. I actually shied away from the initial offer — I started as VP Analytics & Optimization — because there wasn’t an existing team to manage, and I loved managing teams. That said, I knew I could have an impact on the business and took a leap of faith that I would chart my own course. About 18 months after joining Sailthru, I took on our broader client services team (everything post-sale), and after three years running those teams, I took on an expanded role as our Chief Commercial Officer, ultimately overseeing our new business/sales operations in addition to our existing customer base.

What pain point is your company solving?

Sailthru is in the business of helping brands speak to their customers in more relevant, personalized ways. We partner with retail/commerce brands as well as publishers/media companies to help them track what their customers are doing across all channels — email, on-site, mobile app, in-store, etc. — and to make that data actionable in their communications with their customers, with the end goal being that every customer could truly have a 1:1 digital experience with the brand. This is particularly exciting for me as an end consumer myself; I see the challenges brands face with personalization through my own experiences. For instance, I typically do my online shopping after 10pm, yet somehow my inbox is only ever inundated with offers at 7am. There are certain brands from which I only ever buy in-store, and despite providing my email address at the checkout counter every time, the brand’s follow-on messaging to me speaks to me like they don’t know me at all. The fact that our product capabilities ultimately influence every end consumer of a brand is super fun for me.

What do you wish you had known earlier in your career?

Opportunity is not always obvious (in fact, I’d say it’s generally not at all obvious) — so be everywhere, learn everything you can, and create opportunity where it seemingly doesn’t exist. Several years ago, a mentor of mine challenged me that I did not have a “big enough slice of the pie” in a role, and encouraged me to think about how I could take on additional peripheral responsibility. I identified areas of opportunity I felt strongly about — and where no one else was spending time/energy — and charged forward on those to make a bit of a splash. It is critically important to realize that more often than not, you are creating the opportunity for yourself through your passion, drive and willingness to take on the ugly stuff.

Give us one piece of tactical advice (small or large), as a page from your enterprise tech playbook — that you would give to another woman considering a career in enterprise tech?

Be maniacally focused on your customers at all times. If you put all of your energy into making your customers successful, it will be near-impossible for you to fail as a leader (and for your business to fail as a business!). I meet with at least one customer every single day (and many days, will meet with four or five), and it makes me better at everything I do: I better contribute to our executive team meetings, I better empathize with our internal front-line teams, and I better strategize/plan around what the future needs to look like for our products and our teams.

What do you love about enterprise tech?

I love the pace of change in enterprise tech, and particularly revel in the fact that new players have an opportunity to compete and win purely on execution. As someone who previously sat in the client seat, I also love that all B2B players are being forced to focus more on value creation and differentiating on that dimension. At Sailthru we like to push our clients/prospects on the importance of ROI and lift vs. feature bake-offs and workflow tweaks. The Challenger Sale is alive and well, and I love it.

What do you wish would change?

I would love to see more women embracing data analysis and broader quantitative skills. I am a bit spoiled on this front in that I got a really top-notch primer in all things finance, Excel, etc. from an analyst training program at Citigroup at the start of my career, but this is also something that can be learned on the job, and was definitely a skill set that I evolved through on the job experience in other roles outside of banking. For instance, I learned the art of cohort analysis while working at in the mid-2000s; this is something that never really came up my banking work. I consistently see women — even at the manager/director level — shying away from meaty analytical projects and focusing on surface-level data and general trend lines. I truly believe that my ability to translate data into business execution is absolutely what has fueled my career growth.

Is there anything else you’d like to share?

  1. Work your ass off. Pardon my French, but this is hugely important. If I think back to the jobs I had in my 20s, I clocked ridiculous hours and aggressively sought face time in a pursuit to get more work and projects, and it paid off. It constantly amazes me how often people are looking for the next step of their careers when there is still plenty left to challenge the status quo in the current role. Yes, work-life integration (yes, I’m a big fan of alternative words to “balance”) is important, but if you’re invested in building a dynamite career, you must be willing to make the time investment that will yield it. The best career advice I ever received was actually indirect advice; when I was in high school, my father became terminally ill and announced that he needed to scale back his hours (he was also a business executive), at which time his boss told him that “50% of Bill Young was better than 100% of anyone else.” This line has been a guiding principle for me throughout my career.
  2. Trust the process. (Full disclosure, I stole this line from my favorite SoulCycle teacher, but I use it all of the time now.) Leadership teams have to make really hard choices sometimes, but you must assume positive intent and trust that things will always play out, even if not immediately. I can’t tell you how many times earlier in my career I would find myself really frustrated with a top-down business decision, only to completely respect that decision two years later.
  3. Be resilient. Being part of high-growth companies means that change is constant, and oftentimes that change will be uncomfortable. Every time I have managed through a difficult time, I remind my teams that if they give up now (then), they will not build muscle memory around how to navigate through challenge, and thus will stunt their own paths. I remind them that anyone who believes her company does not have challenging times is working at a company that is not transparent (or alternatively, working at a huge company and very far removed from leadership). We have a “no hangovers” rule on my team at Sailthru; when we navigate tough times, we acknowledge and respect them and then we move on.
  4. Do not confuse people management and leadership. It is very common to hear people asking for people management responsibilities after 12–18 months in an individual contributor role. Yes, people management is a great path for some people when the time is right, but it is not the only way to showcase leadership, and it’s certainly not for everyone. I regularly call out examples of individual contributors in our company who I think are some of the best cross-functional leaders we have on board.

Connect with Cassie on LinkedIn and Twitter.

See our Database of Founders of Enterprise Startups (Who are Women) and let us know if we missed someone!

Know a woman leader in enterprise technology whose story we should feature?We’d love to hear from you.



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Work-Bench is an enterprise technology VC fund in NYC. We support early go-to-market enterprise startups with community, workspace, and corporate engagement.