When Dan O’Connell stepped into the CEO role at Front, a customer service platform with nearly 9,000 customers and nearly $100M in revenue, it wasn’t his first rodeo. Having previously taken over from the founder as CEO at TalkIQ (pre-revenue), Dan brought to SaaStr Annual his valuable insights about managing change at different company stages.
Dan shared four practical tips for leaders stepping into new roles – whether as a CEO, executive, or first-time manager. Here’s what he learned about driving effective change while preserving company culture.
1. Take a Step Back and Listen First
While the natural instinct when stepping into a new role is to immediately drive change, Dan emphasizes the importance of listening and learning first. At Front, he made it a priority to connect with the company’s “OGs” – the roughly 60 employees (out of 300) who had been with the company for over six years.
“The worst thing I can do going into a business is dictate ‘this is the way forward,'” Dan explains. Instead, he focused on understanding the existing culture’s propensity for change and identifying potential friction points before making moves.
2. Start with Operating Cadence
When ready to implement changes, Dan suggests starting with operating cadence – small adjustments that can make a big impact without major disruption. At Front, this meant shifting from bi-weekly to weekly forecast meetings. “These changes don’t have to be big restructures or new projects,” he notes. “Sometimes it’s simply changing how the business shows up and manages itself.”
3. Build Momentum Through Small Wins
Leading a venture-backed company is like “playing in the professional sports league,” according to Dan – high pressure, high expectations, and high rewards. His strategy? Focus on celebrating small wins consistently.
At Front, this means highlighting successes during all-hands meetings and weekly emails – whether it’s a successful renewal or winning a competitive replacement deal. “Momentum is incredibly hard to build, but once you have it, it’s incredibly easy to maintain,” Dan shares.
4. Embrace Radical Transparency
One of Front’s most distinctive cultural elements is its commitment to transparency. The company shares its complete, unedited board deck with all 300 employees after each board meeting – a practice that initially made Dan uncomfortable.
When he attempted to scale back this transparency, the pushback was immediate. A colleague’s feedback became a crucial lesson: “If you make a change and there’s more questions that come from it, it’s probably not helpful for transparency.”
Dan quickly reversed course, learning that trust in employees typically rewards itself. “We’ve never had a leak of information,” he notes. “This transparency allows us to have much more practical and real conversations about managing the business.”
Key Takeaways for Leaders
Remember these three fundamental pieces of advice:
1. Don’t Assume Anything: Get into the details, ask questions, and help people understand why you’re asking them.
2. Trust Your Gut: As you mature as a leader, that intuition becomes more reliable. When something feels right or wrong, act on it.
3. Make the Job Your Own: Whether you’re a CEO or a first-time manager, view your responsibilities as a blank check to operate and execute in your way. Share ideas and take ownership of your role.
“You should make your job the job that you want it to be,” Dan concludes. “I never want to look back and say, ‘I wish I had acted on that.'”
