Women in Tech: Whitney Bennett, VP of Talent and Culture

In today’s rapidly-evolving career landscape, many of us can relate to taking a job in an industry completely unrelated to our college degree. Whitney Bennett can say she not only forged a career in a field different from her educational background, she navigated uncharted waters to build a thriving human resources department where none previously existed. For a woman in tech, this is no easy feat.

After earning a B.A. in Marketing from Kennesaw State University, Whitney took a job in sales at telephony startup Vocalocity. “My first job out of college was in sales and taught me that I hated sales,” Whitney recalls with a laugh. “It was pretty early on that I decided to go down the HR path.”

When observing the aura of confidence Whitney carries with her, you’d be surprised to discover that she began her career in HR just seven years ago.

The initial support she needed to carve out her path in the industry came in 2011, when Whitney was hired as the 50th employee at healthcare IT company Ingenious Med. “Mike Vandiver was CFO at Ingenious Med. He came into the role of CFO while I was on maternity leave. Prior to that, I reported directly to the CEO. When I came in as the HR coordinator, Mike easily could have said, ‘I just got here, I need a strong HR business partner.’ But he didn’t do that. He connected me with someone outside of the company to mentor me. He had the company pay for me to go to conferences. He never made me feel stupid, and I learned about the finance side of HR as well. He’s someone I still talk to now.”

Her philosophy for what HR should provide a company was formed during this fundamental stage in her career. “Initially, I probably had the same view of HR that a lot of people do – it’s like Toby from The Office and no one wants to talk to you. It’s bad and scary. But when the company makes HR a partner, that team can really empower people. If companies just use HR to hire and fire they won’t find that type of success. I learned that HR really is about the life cycle of the employee.”

Under Mike’s mentorship, Whitney built out a full-scale human resources approach –– experience she brought to CallRail when she joined the team as Director of Talent & Culture and has since moved on to become the VP. At a rapidly growing tech company like CallRail, Whitney’s first priorities have been implementing a human resource management system (HRIS), Namely, to manage payroll, benefits and departmental organization, as well as introducing new methodologies for goal creation and performance reviews.

“When you come into a new company, there are certain things you know need to happen in order to scale effectively. At CallRail there was no HRIS. It was hard for people coming in to know who people were reporting to. It was clear we needed performance reviews and to create a way for employees and managers to have their voices heard.” Empowering her team to implement Namely gave the opportunity to streamline things like payroll, org charts, 360 reviews, compensation changes, and goal progression.

Rolling out an Objectives and Key Results (OKRs) program was a second significant initiative. Whitney observes that the traditional annual review process is largely outdated, especially in a results-driven work environment. “I wanted the company goals to be very clear and to help employees feel ownership over their roles in relation to them. I wanted managers to have conversations once a month with employees about their progress. OKRs have worked well for tech companies in the past. Google was the first one to do it. At the end of the day, it’s someone’s body of work and I want people to be able to look at that and then correct if needed.”

It can be argued that an HR role is one of the most challenging roles at a startup. Processes need to be established, systems must be implemented, and at the end of the day, the culture that made the company such a fun place to work to begin with has to be preserved. Whitney believes that ultimately, culture is something that needs multi-level buy-in just as much as the product a company is selling.

“I think a big thing, in the beginning, is trying to figure out what your culture is and starting traditions. What are you going to do on a routine basis to put your work away and come together as a company? As you grow, keep the traditions. Don’t let them fall by the wayside. We do quarterly outings now, and that may have to change to twice a year as we grow. But also empower managers. Help people have an environment where they can ask leadership hard questions and it’s OK to answer them.”

How is it possible to bring all these things together into a cohesive plan for scalable success? Whitney’s advice to tech companies is to bring HR on earlier rather than later. “I think HR is often an afterthought and something that companies don’t hire until something happens and they need it. To have sustainable growth you need structure and policies in place. I think if people realized HR is not the bad guy and there to ruin the fun, but instead to make it not so messy as you grow, it would be a huge benefit.”

HR teams fight a lot of hard battles behind closed doors, both to protect their company and to advocate for employees. Whitney is no stranger to going to bat for others, or to the challenges that often face women working not only in tech but in HR.

“I do think it’s important to start STEM young in schools with all children. I think hopefully we’re driving towards a point where it’s not about men and women, it’s about the most qualified person for the job. I hope that’s where we get as an industry. Tech has historically been seen as a boys club, but you can’t market to just men.”

As a woman who has successfully navigated career building and growing her family simultaneously, Whitney is passionate about removing barriers for other women hoping to do the same.

“We’re not our parents’ generation – a time where many women stayed home and raised the babies. In my friend group, most of the women are the breadwinners. Women are going back to work after children and most families have two incomes. I think the whole industry needs to start to be more flexible if they want to grow. At CallRail we recently changed our maternity and paternity leave. Startups are growing up and people are getting married and having kids, both male and female, and tech companies need to make sure they are catering to those people.”

Whitney’s commitment to both the company’s success and the employees’ well-being is what sets her apart as an HR professional in tech. In a sector often understood to be numbers driven with a heavy emphasis on scaling quickly to go public, she focuses her energy on creating a strategic vision that bridges the gap between goals and human connection, allowing for holistic growth of the company as a complete unit.

If you’re interested in learning more about CallRail and joining our team, head over to our Careers page — we’re growing fast!