Insurgence Group — Strategy. Innovation. Leadership.
Guest InterviewEpisode 2854 minAccelerated Execution

Bad News Fast: Building an Insurgent Culture as a First-Time CEO

with Rob Lawrence
Spotify
Apple Podcasts
THE CONVERSATION

Rob Lawrence left 15 years in consulting to run software businesses. Last year, he took the CEO seat for the first time at hospitality-tech firm Otelier. In this conversation, he and the hosts discuss the reckoning coming for SaaS (“every SaaS CEO should be terrified of what AI could do to their business”), why 90% of AI programs fail, and what a first year in the chair actually teaches you.

The tension running through it: the same speed that’s disrupting his industry is the thing he wishes he’d shown more of himself. “Good news fast. Bad news faster.” He also names one regret that surprised him.

Transcript and chapters coming soon.

KEY INSURGENT MOVES

What to take from this episode.

  1. Start with the pain, not the AI. Rob challenges the cost-cutting mindset behind most AI programs. Don't ask "where can we cut costs?" Ask "where's the pain, and what use case can AI solve?" It's the numerator, value creation, not just the denominator.
  2. Good news fast. Bad news faster. Rob deals only in hard decisions and bad news. The easy calls never reach his desk, so he's trained his team to surface problems early, while they're still small enough to address.
  3. Make failure safe, or the bad news stops coming. Matt and Rondo push Rob on the tension between accountability and openness. His answer: celebrate failures like wins. If people fear the consequences of failure, they stop surfacing problems.
  4. Indecision has a cost. Rob's one regret from his first year as CEO? Not moving fast enough. "It took too long to make the call on a couple of things." Delaying a hard decision doesn't eliminate its consequences.
THE GUEST

Rob Lawrence

CEO, Otelier

Rob spent 15 years in consulting before moving into operating roles, including growth strategy at LogMeIn (which he helped take private) and COO of a SaaS workflow-automation business. Last year he became CEO of Otelier, a hospitality-tech firm, for the first time, which makes him a candid guide to both the AI reckoning facing SaaS and what the first year in the chair really teaches you.

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