The path to profitability & Dena’s value framework for evaluating career moves: Dena Upton (Head of People, Dandy)
Listen to our recent episode with Dena Upton, Head of People at Dandy.
We talked about the value framework that she uses to evaluate big career moves, building out the employee value proposition at Dandy, and how their path to profitability is providing employees with more career equity.
Read the highlights below. ??
1. Use this value framework when considering a new People Leader role ?
Dena has a set of values that she looks for when considering a new People Leader role. She specifically looks for five things:
1?? Strong values must be deeply embedded within the organization, and the founders should be able to clearly express those to her.
She saw this with DC and Elias at Drift. She remembers discussing Netflix's culture, Patty McCord's talent philosophy on treating employees as fully formed adults, the importance of rigor, and extreme transparency.
Similarly, when she spoke with Tony and Dan about Dandy, they were able to articulate their values and how these influence their decision-making.
2?? She values decisiveness paired with speed and vision.
“When I was talking to them [the founders] about the Dandy master plan, the data and the words that they were using were emphasizing decisiveness with speed and vision.”
3?? It's important that the founders are prepared for a “no” from her.
She says the relationship with your fellow leaders should be based on mutual trust and respect.
Her numerous conversations with Tony and Dan, whether over dinner or on the phone, showed that they were looking for that.
4?? The team needs to be fearless in facing the truth, even when it's tough to hear.
She wanted to ensure that their approach to truth was data-driven and rigorous.
Their intense OKR process mirrored the approach they desired for the people function, which was important to her.
5?? Servant leadership and “carrying the water” is crucial. Her leadership lessons from David and Elias made her look for the same philosophy in Tony and Dan.
The more they talked, the more excited she became.
Not everything was in place from the start, but the foundation was solid.
Ensuring that foundational integrity was there allowed her to believe they could tackle everything else that needed to be done.
2. Be clear about the repellant aspects of your culture upfront ???
“Our managers use a specific value framework as the backbone of how we discuss culture throughout the company. This approach also acts as a filter—our pace is incredibly fast, and for someone who prefers a structured environment, this might not be the best fit.”
However, Dena says that's perfectly fine. They’re upfront about this during the hiring process, making it clear what to expect.
If someone thrives in ambiguity, feels drawn to challenges, and finds being slightly out of your comfort zone appealing, then Dandy might just be the place for them.
They discuss this openly in interviews because while it's an aspect of their culture that attracts many, it might deter others.
She says it's important to be transparent about that from the get-go.
3. Dandy's path to profitability ??
Dandy is on track to meet its profitability goals, aiming to reach this milestone by late spring.
Dena indicates that this progress will eliminate the need for further fundraising. She notes that by May, they're also set to achieve their contribution margin targets, marking a significant turnaround.
When she joined, the company's contribution margin was at a negative 20%, but they've managed to flip that to a positive 21%.
She attributes this 41% improvement to the hard work and dedication of everyone at Dandy.
Now, not only is Dandy profitable, but it can also reinvest its earnings into innovation and enhancing the company's efficiency without depending on external funding or market conditions.
Their focus on customer satisfaction, efficiency, and swift service has set them apart, making Dandy a rare example of a young, profitable company.
This achievement has rightly won the admiration of Dandy's board.
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Dena's definition of a Modern People Leader (from lens of leading a diverse & globally dispersed team) ??
"I think it's listening to your diverse employee base and making sure that your people practices are not biased against any particular group of people. It's making sure that you are giving your people practices the oxygen, sunlight, and measurement to make sure that you're not favoring one pocket or group of people over others."
The career advice Dena would give to her 22-year-old self ??
"Startups thrive on relationships rather than hierarchy. The key is to immerse yourself in a rocket ship organization. When it comes to interviews, the questions will revolve around your achievements, not your title. Choose a growing company and focus less on rapid promotions. Being integral to a hyper-growth journey matters more in startups, which are inherently relationship-driven."
See you next week!
P.S. Check out The Distributed Work Report by MPL alumnus Shelby Wolpa. It's filled with surprising and counter-intuitive insights from 277 distributed companies worldwide.