TecHRseries Interview with Dena Upton, Chief People Officer at Drift

Teams that do not have the right talent during a downtime will find it more challenging to sustain than those that do. This is where HR leaders need to realign efforts and understand the core needs of their business and fit the missing (talent) pieces in time to help companies drive business outcomes in a challenging environment. Dena Upton, Chief People Officer at Drift shares more in this quick chat with TecHRseries.



Welcome Dena! Tell us a little about yourself …what are some of the biggest moments you look forward to being in HR and Talent Management?

Thank you for having me! I joined Drift in October 2018 as the company’s first Vice President of People — and was elevated to Chief People Officer in February, where I continue to oversee talent acquisition, human resources, and diversity and inclusion initiatives.

I’m used to startups — I was at LogMeIn before Drift, and a handful of tech startups in Boston and San Francisco prior to LogMeIn but some of my favorite efforts have revolved around the exciting and unique challenges of running people operations for a company that’s growing as fast as we are. At the start of 2019, Drift had 249 employees. Today, we are nearly 400 employees strong across four national offices. I think we can attribute a lot of this growth and success to our values, which prioritize customer centricity, extreme ownership, a bias for action, and a culture of respect.

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Another big contributor is our continued effort to build a diverse and supportive workplace. We’ve worked to establish Employee Resource Groups (ERG), which are employee-led groups to support people of similar backgrounds or interests. This focus on growth, our values, and inclusion efforts were a big reason why we were recognized by Inc. Magazine as an honoree for their list of “Best Workplaces” in 2020.

We’d love to hear a little about life at Drift during the pre-Covid-19 days and in what ways the team is adjusting to the new normal now?

Before the pandemic up-ended how we work, Drift had a very “in-office” culture — and it was intentional. Our founder and CEO had experimented with a hybrid culture in the past and felt like inevitably those who were remote would miss out on key information, couldn’t fully appreciate the culture and weren’t able to easily relate to and communicate with their co-workers.

We also relied on unique rituals designed to bring the team together on a regular basis. For Drift, these rituals include “Monday Metrics” where teams gather to examine progress in key areas and “Friday Show and Tell” where the entire company comes together to recap the week and share results and accomplishments.

When the pandemic hit and our office was forced to work remotely in March, we had to quickly transition our culture – and our nearly 400 employees – to meet the new demands of remote work. Part of this effort has been translating our rituals to new, virtual platforms. We held our 2020 Second-Half Kickoff event, virtual, we still make sure that “Monday Metrics” and “Friday Show and Tell” still occur weekly — and our weekly “Inside Drift” newsletter keeps everyone informed on important company happenings, future events, and includes fun pictures of our teams working from home

While we’ve all missed the energy that usually comes with these events in-person, we’ve tried to ensure they are all as interactive as possible.

Drift has also relied on employee engagement programs designed to build camaraderie and connect our remote workforce. Recently, we held a virtual “Friends and Family Day” for our entire company, where the team had the opportunity to connect outside of a business setting. In addition to large team functions, our ERGs and other teams have organized “Inside Drift” events, including trivia nights and cocktail-making classes where team members can break out into smaller groups.

More than anything, we want our team to continue to grow and learn, so we’ve transitioned our mentor series to a virtual event. Thus far we’ve had investors and advisors, like Pat Grady from Sequoia, Molly Graham from Social Capital, and Larry Bohn from General Capitalist come and speak with our team.

We’re also big believers in transparency, and believe it’s important for everyone to understand what and why we do things. To aid that, we’ve also held “SLT At Home,” events where our employees have a chance to ask important questions to our senior leaders and executive team about all company matters, including the return to office and business development efforts.

The new normal is redefining a lot of things in business; even the role of HR – how according to you will the role of HR heads in tech / B2B change from here on?

I’ve always said that good HR teams need to fully understand the business — but this is so important now. HR leaders need to make sure that everyone on their team commands a deep understanding of the business, especially when things get technical and complex. Teams that don’t have the right talent in place for the next 6-12 months will fail — and if the HR team isn’t working on this now, they will fall behind.

How do you see this pandemic impact the global talent and work marketplace in tech / B2B? What top tips would you share with job seekers and HR teams who are on hiring sprees during this time.

I believe we’re all much more comfortable with remote work now than we were six months ago, and behaviors are shifting as a result. We’re already witnessing people move away from larger cities en masse. I think this new exposure and comfort with remote work will lead companies to embrace the global talent pool. Moving forward, HR teams can lean on remote work as a permanent fixture of talent acquisition long after our return to the workplace, whenever that might be. There are inherent benefits to businesses with that perspective: One being that we can focus more on who a person is, rather than where they are.

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Broadly, I would say the best tip I can offer HR leaders right now is to continue to think outside of the box and find fun, informative, and engaging ways to bring your teams together. I think we’ve all learned over the past few months that there are only so many Zoom happy hours we can sit in on. It’s up to us, now more than ever, to build that sense of engagement.

What according to you makes for the ideal HR Tech stack – in B2B what HR technologies would you advise HR teams to adopt?

This varies widely depending on the size and type of organization you are in. For us, we will continue to lean on workplace communication tools like Zoom, Slack, and Asana to manage productivity and connect us day-to-day. For HR-specific tools, we are in the process of evaluating our performance management and engagement tech stack to simplify things.

Just as important as tracking processes for new hires are conducting regular check-ins with our teams to make sure they are feeling supported. At Drift, we use TINYpulse, an employee engagement and feedback software, that allows us to share brief surveys with our teams. This tool also allows employees to anonymously submit questions and comments to our leadership teams. We combine these ongoing efforts with our employer Net Promoter Score (eNPS), a quarterly effort we make to have employees rate our performance. These checks and balances have been an essential process for us remotely.

A few general thoughts / tips for businesses worldwide dealing with the current world pandemic?

My overarching thoughts and tips are simple: lean on your values and focus on transparency. By doing these things, you can most definitely build a workplace that’s built to withstand remote work and any other challenges. At Drift, we’ll continue to embrace our employees’ curiosities, and provide the resources for them to grow while they work here.

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Drift is the Conversational Marketing platform that combines chat, email, video, and automation to remove the friction from business buying. With Drift, you can start conversations with future customers now, on their terms — not days later. There are over 50,000 businesses that use Drift today to generate more revenue, shrink sales cycles, and make buying easy.

Dena Upton is the Chief People Officer at Drift, where she leads the people operations team, responsible for the company’s talent development, operations, recruitment and retention. Prior to Drift, Dena served as VP, People and Talent at LogMeIn. Under Upton’s leadership, her prior companies have been recognized for outstanding culture and talent management, including nine consecutive Best Places to Work accolades for LogMeIn from the Boston Business Journal.


Chief People Officerdiversity and inclusionDriftEmployee Resource Groupsextreme ownershipHR Technologyhuman resourcesInc.InterviewsJob Seekersremote workforceTalent Managementtech startupsvirtual platformsWorking From HomeZoom
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