Women in Enterprise Technology: Allison Pickens, Chief Customer Officer, Gainsight

April 10, 2018

The Women in Enterprise Technology series features profiles of some of the top women leaders in enterprise technology from the Salesforce Ventures portfolio and the larger Salesforce ecosystem. The goal is to showcase the fantastic work these women are doing at their respective organizations, and to encourage more women at all stages of their careers to consider enterprise software.

As CCO of Gainsight, a customer-success software company, Allison has a lot of different roles, but one is to be a role model for the industry. She also acts as a role model to women in enterprise technology generally, hearing from women inspired by her to pursue executive-level jobs in a male-dominated industry.

Her path to customer success wasn’t direct. From management consulting at Boston Consulting Group to private-equity investing at Bain Capital, she saw how businesses work with an investor’s sensibilities. “It gave me a lot of perspective on how value is created in businesses,” she says. She discovered she had an entrepreneurial bug and went to Stanford Business School with the intention of starting her own business. Which she did with Spark Trades, a kind of LinkedIn for blue-collar workers. Eventually she met Nick Mehta, the CEO of Gainsight, and came aboard at an early stage, helping to build the company into a market leader over her four years.

We sat down with Allison to talk about the changing nature of customer relationships, making lists of self-criticisms, and whether she thinks of herself as having a “female” style of leadership. (Spoiler alert: She doesn’t.)

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What drew you to enterprise tech?

To be honest, growing up, I never saw myself as someone who was likely to be in business. I studied mostly philosophy in college at Yale and thought I’d pursue a career in public service some day. But since I was a teenager, I always found myself mobilizing people toward what I perceived to be a greater goal — whether it was developing a group of nice friends in middle school (in a typical middle school environment that wasn’t always nice!), giving motivational speeches to my high school lacrosse team, or building new campus organizations in college, such as the Women’s Leadership Initiative that’s still around today. When I came across Gainsight over four years ago, I realized we had an opportunity to grow a community that advocates for a new paradigm for how we support our customers. In general, I’ve always loved building movements that have a greater moral goal. I think of my personal purpose — or “telos,” to use a term from Ancient Greek philosophy — as leading movements to build ethical communities.

In enterprise technology, I think that we have a big opportunity to create a different way of doing business that puts our customers and teammates first. And at Gainsight, the purpose of our company is to be human-first. It’s a powerful message.

How do you think customer relationships, particularly facilitated by sales, marketing, service, social, and so on, will change in the near future?

The old frameworks that people used to use to understand how companies make money don’t apply anymore. The one that people used to talk about, particularly in the ’90s, was the marketing and sales funnel. We would start out with a bunch of leads, convert some of those leads to opportunities, convert some opportunities to closed deals. And then we could just maintain our customer base in some basic way with reactive customer support.

The next model of revenue growth was the hourglass. People recognized that you had a huge expansion opportunity in your installed base of customers. Once you acquire a customer, you can grow revenue from it. But even that model is a little bit outdated now because companies that are trying to grow the fastest and the least expensively are realizing that if you can get your customers to sell for you, you can build pipeline. And, if your customers are not advocating for you, you have a pipeline problem.

The third model of revenue growth and the one that we’ve embraced at Gainsight is the Helix Model. It says that if you acquire a customer and you make that customer successful, that successful customer can pave the way for three new leads — first, a lead for a renewal; second, a lead for expansion; and third, a lead (or multiple leads) for new logos, when that successful customer advocates to prospects for your product or service. That way we can “close the loop” on customer acquisition and ultimately extend the size of our company upwards, which is why we end up with the spiral of growth — the helix.

Customer relationships from the vendor’s perspective are going to change because vendors now see their customers as actually being a source of new pipeline. It’s now a company imperative to generate outstanding outcomes and experiences for your customers. It’s no longer optional.

How do you think about the issue of women and leadership in the context of your own career?

I’m not sure I have a brand of leadership that I would necessarily call “female.” I’m not even sure there is a “female” brand of leadership. So all the men out there, I wouldn’t underestimate your ability to be a role model to the women who work for you. I see myself as a leader who happens to be a woman. I’m a person first of all, who has a certain personality and set of values, I think that informs a lot of my approach to what I do.

At the same time, I do consider myself a feminist — not in the militaristic sense that is often ascribed to the word, but rather in the sense that I believe in empowering women. To me, that’s a part of servant leadership, which is the philosophy that I try to hold myself to.

Philosophy aside, I do believe that given all the obstacles that women face out there, managers need to proactively monitor the environment for women on their teams and create a culture that sets them up for success. I say “need to” because unless a manager does this, they’ll inevitably lose the women on their team. I’ve seen it happen many times in our industry. It’s a competitive hiring market out there.

So I consider it a huge competitive advantage of ours at Gainsight that we have a number of women in leadership in my Customer Success team, that our highly successful VP of Enterprise Sales is a woman, that we have several women on our executive team, that we have a board director who is a woman, and that our CEO and my boss Nick Mehta cares deeply about reducing bias and creating change. At the same time, we have gaps. We always have more work to do. I want us to do better every day.

What advice would you give young women who are entering the workplace?

I think women over the course of their lives receive so many signs from the world that they’re not good enough. For me, those signs have translated into a lot of self-criticism. I find in talking with other women in the industry, it seems to be a pattern that we’re very critical of ourselves. For our benefit, I think we need to fight that. I started keeping a list of all the self-criticism that tends to go through my head. That way I externalize it for myself, and I recognize it as being a voice that I don’t want to listen to. It’s helped me to preserve my peace of mind and free up mind space for things that are helpful for me.

Also, I notice that customer success as a function tends to have more women than any other functions within enterprise-software companies. I think that the success of the customer-success function can pave the way for the success of women in enterprise technology generally. Perhaps this is the niche where we’re starting to get traction.

In the last couple years, what have you noticed in terms of women in technology?

I think a lot of chief customer officers will go on to become CEOs of enterprise software companies, and because there are many women in customer success and chief customer officer roles, I think that increasingly we’re going to see female leaders of software companies. Another trend that I notice is that women are increasingly not settling for working for people who are not supportive of them. There are great bosses out there — better to go find them! I think with those two trends combined, we’re going to see a lot of progress for women in the next few years.