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.
Deepa took what she calls a “non-traditional path” through her technology career, one that, incidentally, had a brief stop at bagels.
An early engineer at Salesforce, Deepa left to study the intersection of internet and law at Harvard Law School. After practicing technology law in San Francisco, she discovered in working with her clients an entrepreneurial streak. She directed that into opening Schmendricks Bagels. (“This will probably be the most interesting thing I ever do, conversationally, at least,” she says.)
She ran it lean, like a startup, and while it was a popular and award-winning endeavor, health concerns (she found out she was gluten intolerant!) pushed the team to close after three years. So she went back to technology, “which is really my first love.”
In 2014, she founded Wootric, a modern enterprise feedback management company that helps businesses measure and increase customer happiness. Wootric tracks customer experience metrics like Net Promoter Score and uses AI to classify and extract insights from feedback, “so everyone in your organization can align around the Voice of the Customer.”
We talked to Deepa about how she arrived at Wootric, and what she learned along the way.
You took an interesting route to land where you did.
It’s been a circuitous journey! But I think everything I’ve done along the way has really prepared me to be a good CEO. I’ve learned to be resilient in the face of all kinds of obstacles — from crashing stock markets and layoffs, to barley shortages, to Y2K (remember that? We now have GDPR). I’ve learned to work with people of different backgrounds — for example: every industry has its own unique way of coping with on-the-job pressures, be it buttoned-up lawyers (irreverent blawgs), food-industry veterans (cooking for each other), or tech teams (retrospectives). I’ve learned to be agile and to constantly innovate in my space because customers deserve that.
What drew you to enterprise tech?
My Salesforce years were very formative; they helped crystallize my passion for the business user and the business buyer. My instincts around building product and building culture are all a direct result of that Salesforce experience. I trained myself to listen for problems that business users face — if you asked me to build a company and a product for consumers, I’d probably be a little lost. Even my bagel company, while it was a very popular consumer brand, actually made a profit catering to other businesses. So I think there’s something in my DNA — I really seek out the problems of the enterprise customer.
Did the bagel biz teach you anything that you applied to enterprise tech?
The one thing I found invaluable at Schmendricks was when someone bought a bagel, bit into it and gave me feedback right then and there. I thought why don’t businesses take the opportunity to get feedback from customers while they are engaged with the company’s product?
There’s something wonderful about the customer relationship because everybody I know loves to give feedback when it is easy to do. Channeling that — asking them at the right time and the right place, using that opportunity to build a relationship — was a lightbulb moment for me.
What’s one of your personal strengths as a CEO of an enterprise tech company?
I focus on people. Your product must create value and delight, but to build a business (especially around the enterprise) it’s all about your customers, your partners, and your team. Wootric has earned the trust of companies like DocuSign, Zoom, and VMWare because of the focus I place on ensuring that the people who use our product are successful. I’ve also prioritized relationship-building with partners like Salesforce, Gainsight, and Intercom. That has paved the way for native integrations and co-marketing that benefits the mutual ecosystem. Finally, my co-founder and I have been extremely thoughtful about hiring for culture. Our team members are subject-matter experts but also share our values of integrity, curiosity, and passion for the customer. As a result, we have a fantastic CTO, head of sales, VP of marketing, and so the only thing left for me to do is to guide the ship as CEO.
Tell me about the idea of customer happiness, and how the relationship with the customer is changing, as a result of technology.
The relationship between you and your business customer is driven off of delight and modernity. Companies that do this best have a competitive edge. Your customer today is hyper-connected and expects an experience with their business tools that is as seamless and delightful as their consumer apps. So if I make my way to work using an app as intuitive as Lyft, I’m not going to be thrilled about spending an afternoon with business analytic software that feels like it’s from 1999.
It really is the consumerization of the enterprise experience. Let’s be honest, the era of a 15-question e-mail survey, or the intrusive, annoying pop-up in the middle of your work screen — that era is over. Customer-centric survey design is essential.
And customer feedback, the cornerstone of measuring happiness, is now everywhere.
Your customer is engaging with you in a chat box, in online forums or on social media; so the modern customer-feedback platform needs to have the nimbleness to engage with your customer, wherever they are. It also needs the technological prowess to make sense of the enormous amount of feedback that’s coming at a business from so many sources. Wootric has invested in machine learning because AI-driven software is required to provide the deep insights that companies need to keep up with evolving customer expectations.
Have you had any “Aha!” moments in your career?
In my late twenties, I realized that you get to define what your career is, and what it means to be successful. When I was contemplating starting a company, I had the realization that there was nothing stopping me. There is no playbook for success or expectations other than my own. Once I realized this, I stepped back from law to start Schmendricks, and I never looked back. I began to dig into my talents as an entrepreneur. Success flowed from that.
How have the different phases of your career shaped what you think about women and leadership?
I’d never thought about “women and leadership” as an issue as much as it is an opportunity. I think both investors and boards lose out on a very talented pool of leaders when they focus on their good old boys’ networks and tried and true stereotype of what a leader looks like in Silicon Valley.
I think the typical investor still sees merit, or hustle, or success in entrepreneurs that look like Mark Zuckerberg, or talk like Steve Jobs. But neither of those gentlemen, as successful as they are, fit the mold of a category-defining leader in their day — until they succeeded. I think the entrepreneurial traits that are sought after by investors needs to diversify, in the interests of finding that entrepreneur who is an orthogonal thinker and can take the company all the way to a successful exit.
What trends have you noticed around women in tech in the last few years? What’s encouraging? What’s troubling? Where do we need to move forward?
Access to capital is critical in today’s tech industry, and I think everybody has recognized now that the playing field will only level when women invest as much as men do. I think this is trending in the right direction. Every day, the number of women-founded or women-led venture capital firms and angel groups is rising — one only needs to look at AllRaise.org. Wootric itself has benefited from advice and investment from enterprise B2B focused investors like Shruti Gandhi of Array Ventures, Laura Rippy from Green D Ventures, Judy Loehr, Caroline Mizumoto, Rene Yang, and Courtney Broadus. And happily, I see that the trend is positive for founders and investors of color too.
I think the next hurdle is probably a more family-friendly work culture, and this is not a gender issue. It’s true for men and women. We need to be more focused on productivity than on long hours or a party culture.
What advice would you give young women who are entering the workplace, and specifically, in enterprise tech?
Enterprises are all about the long game. You need to keep in mind that one success or failure doesn’t define you. You should take responsibility for your successes and for your mistakes, but don’t dwell on either.
Also, build deep friendships outside of your industry. Enterprise technology can be a little bit of an echo chamber, so it’s good to get perspectives from the outside.