Run the Numbers, March 10, 2025:

Uncovering Blind Spots and Other Lessons from High-Growth Companies with Five-Time CFO David Lapter
Host: CJ Gustafson | Guest: David Lapter, CFO at Dashlane

Episode Overview

In this episode, CJ Gustafson sits down with David Lapter, a five-time CFO currently at Dashlane, to explore the blind spots, operational lessons, and cultural dynamics of high-growth tech companies. David shares candid stories—from missing crucial VAT payments to the domino effects of unchecked execution mode—while emphasizing the importance of humility, strategic prioritization, and authentic competitive differentiation. The conversation is packed with analogies, actionable frameworks, and reflections on how to build resilient teams and finance functions that can scale.

Key Discussion Points & Insights

1. Identifying and Managing CFO Blind Spots

[06:47]–[11:32]

• Blind spots are inevitable and change over time:
  David analogizes blind spots to those in driving—some remain with you for years, while others appear suddenly. CFOs must consistently carve out time to “diagnose and think at different altitudes” (07:50).

• Skillset-based blind spots:
  Both David and CJ admit their weaknesses in hardcore accounting and legal, especially without a CPA background.

  “As early stage CFOs, I think we're all forced to play a lawyer on TV, fake it. But at some point you've got to…put your hand up and say, okay, I can no longer do this.” – David [09:18]

• Delegation and hiring:
  The natural tendency is to double down on areas of comfort (e.g., FP&A) and resist giving them up. Yet, truly scalable growth means hiring leaders—even if it takes two years to fill a role—without lowering the bar.

  “I had one role at Dashlane… that took me almost two years to fill. I'm just happy I never lowered the bar because it's been a game changer for us.” – David [11:11]

2. Prioritization Frameworks for CFOs

[13:24]–[17:10]

• Eisenhower Matrix:
  David credits Mark Suster with introducing the urgency/importance framework early in his CFO career. While not always written down, he regularly forces his team to assess, “Do we have the right balance of short-term and long-term?” (15:20).
• Long-term projects vs. day-to-day:
  Example: Integrating Salesforce and NetSuite is a project that requires carving out long-term bandwidth—otherwise, “you may be afraid of it” and never get to it if trapped in daily crises.

3. Execution Mode: Blessing or Curse?

[21:04]–[26:14]

• Execution mode syndrome:
  A warning from David’s Fab.com days—always being in execution mode prevents stepping back to assess what isn’t working (or what’s festering).

  “A lot of lessons learned…not staying out of execution mode because…cram times will come and go, but they can’t just fester.” – David [21:58]

• The risk of spreading too thin:
  Both agree that focus beats volume.

  “I'd rather accomplish two to three things than accomplish 50% and poorly at that of 10 things…You won't be judged on how many things you accomplish, it's how well you execute.” – David [23:12]

• Defining “done”:
  Misalignment about what “done” means can derail cross-functional efforts, highlighting the need for executive presence and clarity.

4. Talking About Competitors: Respect, Not Demonize

[26:35]–[36:52]

• Respect starts with the acknowledgment of shared passion:

  “Start by respecting the different players in your sector. Know you have more in common than you think.” – David [27:01]

• Collaboration with competitors:
  In cybersecurity, partners like Apple or Google can be both competitors and ecosystem allies (e.g., FIDO Alliance). Small players benefit from uniting for a stronger voice.

• Differentiate, don’t demonize:

  “Demonizing the competition is lazy…real differentiation starts with owning your own story.” – CJ [02:03]; reinforced by David [30:28].

• Story-driven differentiation:
  Focus on the “two or three things around which I can from my heart...tell a story that somebody can identify with” (32:21), rather than endless feature checklists.

• Using competitive content internally:
  Dashlane maintains a Slack channel for competitor updates—not to obsess, but to remind teams to stay vigilant and motivated.

  “We don't only do that for awareness…we do that to remind our teams that our competitors are not complacent…It's a constant race.” – David [34:23]

5. Building High-Functioning Teams in Hypergrowth

[39:43]–[46:42]

• Evolution from generalists to clear swim lanes:
  As companies scale (100–150+ people), roles must become more specific; the “Cheers threshold” (where not everyone knows each other's name) is a key inflection point (41:12).

• Guardrails and cross-functionality:
  Introduction of “offering teams” at Dashlane—cross-functional groups accountable for prioritized initiatives, ensuring all bases are covered and minimizing downstream surprises.

• Domino effects of siloed decisions:
  Classic example: HR making payroll changes that impact finance workloads in ways they don’t anticipate (45:00).

6. The Perils and Power of OKRs

[46:50]–[51:58]

• OKRs: Keep it simple:
  Early efforts at Dashlane failed by rolling out too many OKRs, too fast, and too granular—resulting in operational rejection.

• Focus on a handful of key results:
  “5 KRs not necessary, not allowed…give me 1, 2, 3 KRs…that will help define and align everybody and really rally the troops.” – David [50:11]

• Make metrics meaningful:
  Tie every key result back to something understandable for every employee. A naked OKR without a story or context fails to mobilize action (51:47).

• Beware frameworks-for-frameworks’ sake:
  Don’t adopt what’s trendy (“Google does this…”) if it doesn’t fit your company’s scale or context.

  “Just because you read something or it's worked for one person, that doesn't necessarily mean you need to drop everything and adopt it either the same way or at all.” – David [47:08]

7. Copying Best Practices and the Social Media Illusion

[52:16]–[54:36]

• "Everyone has solved everything":
  It’s easy to feel behind seeing social media and competitor spins, but most wins and learnings come from long, painful journeys tailored to each company.

  “You know the depth and the scale of your warts better than your competitors, but believe me, they're freaking out about other stuff.” – David [53:44]

8. Org Reporting Lines—Should HR Report to Finance?

[55:06]–[57:14]

• Early stage: probably yes. Later stage: definitely no.
  As complexity grows, HR should shift to a dedicated people leader. The risk when HR reports to CFO too long is that “people function can’t be run [as] an afterthought.”
• People is a strategic function:

  “The people function as partners in crime with finance…But I can't do what [our head of people] does and vice versa.” – David [57:22]

9. Lightning Round: Mistakes, Advice, Tools, and War Stories

[58:06]–[67:40]

• Biggest mistake:
  Early career—forgot to include a hundred-thousand-pound VAT payment in a cash forecast (“gave me a big scare, obviously led to credibility issues with the board, but we managed through it” [59:06]).
• Advice to younger self:
  “Listen, but speak up.” Learn to reserve your input until it matters, but don’t be afraid to be the minority voice, especially before important decisions are made ([60:25]–[63:09]).
• Finance software stack:
  • NetSuite (core ERP), Excel dominates FP&A and RevRec, bill.com, Expensify, Vendor, Avalara, and Carta (with a self-maintained Excel cap table as backup).
  • “I'm always going to be more comfortable in Excel than in somebody else's tool...” – David [64:40]
• Craziest expense issue:
  Someone purchased “a million boxes” for shipping at the height of holiday season without informing finance or logistics—triggering chaos and downstream operational headaches ([66:20]).

Notable Quotes & Memorable Moments

• On Prioritizing Growth Initiatives:

  “You won't be judged…on how many things you accomplish, it's just how well you execute them.” – David [23:18]

• On Differentiation vs. Demonization:

  “Demonizing the competition is lazy…real differentiation starts with owning your own story.” – CJ [02:03]

• On Hiring and Delegation:

  “The reality is you can’t give in to the urge of lowering the bar to fill a role…and bringing on a true seasoned leader of FP&A made a world of difference.” – David [11:07]

• On OKR Simplicity:

  “5 KRs not necessary, not allowed…give me one, two, three KRs…that will help define and align everybody and really rally the troops.” – David [50:11]

• On Social Media Illusions:

  “You know…the scale of your warts better than your competitors, but believe me, they're freaking out about other stuff.” – David [53:44]

• On Knowing When to Specialize:

  “There's a point in time…let's call it the Cheers syndrome…where not everybody knows your name and you don't know everybody's name. My guess is…between 100 and 150 [employees].” – David [41:12]

Timestamps for Important Segments

• [06:47] – Identifying and owning blind spots as CFO
• [11:32] – The human tendency to hold on to your strengths
• [14:21] – Eisenhower Matrix and forced prioritization
• [21:04] – Execution mode syndrome and lessons from Fab.com
• [26:35] – Respecting competitors and building authentic differentiation
• [39:43] – Evolving team structures as companies scale
• [46:50] – Making OKRs simple and actionable
• [52:16] – The illusion of best practices and social media comparison
• [55:06] – When HR should (or shouldn’t) report to the CFO
• [58:06] – David's biggest on-the-job mistake
• [63:37] – Dashlane's finance tool stack and reasoning
• [66:20] – Craziest expense: a million unsanctioned boxes

Tone & Style

The conversation blends candor, humility, actionable advice, and personal war stories—delivered with banter, honesty, and the occasional analogy or quip (“let’s call it the Cheers syndrome…”; “I still keep my own cap table in Excel”).

Summary:
This episode is a rich medley of real-life CFO wisdom—blind spots, hiring, prioritization, competition, team dynamics, goal setting, and even expense horror stories—framed with memorable stories and no-nonsense advice for anyone operating or aspiring in high-growth tech finance.