Join Dena Upton, the dynamic force behind Drift's people strategies, as she navigates the transition from a strict office mold to a thriving hybrid framework. This episode unveils:
In episode 6, I had the pleasure of interviewing Dena Upton, Head of People at Dandy and former Chief People Officer at Drift. We delved into the transformation of traditional office settings into flexible, inviting hybrid workplaces. She started off by sharing her experiences at Drift. Drift initially had a strict office-based model before transitioning to a flexible hybrid model during the pandemic. The shift was driven by a desire for diversity and equity, as well as recognizing the importance of in-person connections for training and mentorship.
Dena Upton explained that Drift transformed their offices into "conversation spaces" where teams could come together in-person rather than just conducting more virtual meetings. The pandemic accelerated the acceptance and adoption of remote work, but there was still a need to balance connection and relationship-building with task efficiency. This experience taught Upton that hybrid work is not a one-size-fits-all approach and should be adapted based on the organization's specific needs and customers.
Dena Upton emphasized the importance of employee surveys as a tool for understanding the sentiments within the company. Conducting employee Net Promoter Scores (NPS) can help gauge overall satisfaction and likelihood of promoting the organization as a place to work. Heat maps and pulse surveys can be used to gather more specific feedback on various aspects of the organization.
“I think HR people data is really important. Historically, organizations have relied on anecdotal feedback, but I think ‘measure what matters.’ You can survey people as they’re walking out the door, but that’s too late. It’s really important to meet people where they are, and a way to do that is a regular cadence of feedback.” - Dena Upton, former CPO at Drift
Upton stressed the need to collect feedback regularly. Oftentimes, asking for feedback during the exit surveys is too late. Moreover, she stressed the importance of using data and said that organizations should 'measure what matters.' Companies can build trust throughout their organization by sharing the data and taking action on the feedback.
Dena Upton discusses Drift's survey that assessed employees' preferences for remote, in-office, or hybrid work environments during the COVID-19 pandemic. The survey revealed that the organization was split into roughly thirds: those who preferred working from home, those who wanted to be in the office, and those who were indifferent.
Upton noted that the split in preferences was surprising considering that the initial survey had shown a preference for in-office work, but the pandemic changed people's perspectives and made them unsure about returning to the office. To address this split on preferences, Drift created “Work Wednesdays” and “Work Thursdays,” making the office an attractive space with fun activities and training. The initiative also encouraged employees to be in the office on the same day, creating a sense of community and fostering cross-functional relationships.
“Coming into the office wasn’t a punishment. It was a celebration of our community, and we wanted to reinvest back into the community and our connection with each other, and really double down on the need to invest in relationships before tasks.” - Dena Upton, former CPO at Drift
Upton realized that it would be impossible to please everyone, as individual circumstances and preferences varied greatly. However, the company could try to create communities and connections among those who came into the office. Drift held quarterly team connections and department meetings to foster connection and set strategy, even if they were not in person. These meetings and gatherings served as a way to recharge and reconnect with colleagues.
Dena Upton shared how her current company, Dandy, ensures equity between in-person and remote employees. The decision to go digital-first was based on the principle of ensuring equity and a consistent experience for all employees, regardless of whether they work in the office or remotely. The company wanted to avoid creating a split in the organization and wanted to ensure that remote workers felt included in decision-making and project assignments. In-person interactions with leaders and department-level meetings were available for remote employees to connect with their colleagues and leaders.
Upton explained that they reinforced the principles of digital-first to avoid slipping back into old ways of working, such as having side conversations or making decisions without communicating them to remote team members. The company used data to monitor and measure the fairness of the system, such as the speed of promotions for employees in different locations, and made deliberate efforts to ensure that everyone adhered to the digital-first principles and maintained a fair and inclusive work environment.
“It takes time to make sure that the system is fair, but you also have to reinforce those principles because you can slip back to old ways of working and our general hygiene around team meetings, documentation, or async communication.” - Dena Upton, former CPO at Drift
Dena Upton explained that she stays connected to her team by doing a "Sunday Night Series" where she shares thoughts about the week, books she's reading, and what she wants the team to think about outside of their specific tasks. She records a video or podcast using tools like Loom to send to her team on Monday, or sometimes shares quick snippet videos and one-pagers to keep the team connected and informed. The use of this Sunday Night Series helps her maintain open lines of communication, set the tone for the week, and expose her team to various people-related topics.
Dena Upton discussed the use of Artificial Intelligence (AI) within their organization's HR department. They use AI in the communication process, aiding in interpreting data from various surveys and forming large-scale communication strategies. They also use AI to compare their organization's concerns to those of other similar-sized enterprises. She shared that AI can help sift through large amounts of data quickly, allowing for trends or patterns to be identified, and saves them time in data analysis by automating tasks that would typically be done manually in Excel.
Dena Upton brought up the challenges and benefits of remote and hybrid work culture. She emphasized that creating a hybrid work policy is not a one-size-fits-all situation and proper care needs to be taken while defining a digital-first, remote-hybrid, or in-office strategy, keeping in mind the authenticity and specificity to different organizations. Hybrid work can provide a balance between in-office and remote work, but it requires careful planning and consideration of individual preferences and needs.
“We were very much an in-office company, and then we switched to very much digital-first and sort of 'poo pooed' this idea of hybrid. We were very black and white with the way we talked about it, but the reality is—it’s gray.” - Dena Upton, former CPO at Drift
Making mistakes is part of the process, and organizations should be open and transparent about their strategies and adapt as needed. As she learned from her own mistake at Drift, the shift to remote work is not a one-way door but a continuous journey of adaptation and experimentation.
Jenny is a top Go-To-Market (GTM) leader in the Greater Boston area, where she has a track record of building powerful brands and categories, generating demand (for both sales- and product-led orgs), and creating energizing mission-driven cultures of belonging in the B2B tech space.
As former Chief People Officer at Drift, and currently at Dandy, Dena strives to find new and innovative ways to approach business opportunities and believes in enabling all people to reach their potential.
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