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Frank Fillmann: How I Boosted Revenue by $500M at Salesforce; Tips for Hiring Salespeople | E992

Frank Fillmann is CRO/Country Leader Australia for Salesforce where he is responsible for responsible for the overall strategy, execution, success, and growth of the $1B+ Australian market across all industries. Prior to Salesforce, Frank was SVP/GM @ Tableau where he was responsible for the strategy, execution, and growth of Tableau's Top Accounts. Over the last 10 years at Salesforce, Frank's accomplishments include $500M+ new revenue closed in 5 years and $1B+ revenue managed. As a result, Frank has been awarded #1 Sales VP of the Year, North America, 3 times! Huge thanks to Zhenya Loginov @ Miro for the intro to Frank today. _______________________________________________ Timestamps: 0:00 How did Frank get into sales? 3:54 How do you define a sales playbook? 8:42 How to assemble a top sales team? 12:37 Advice on Hiring Sales Reps 16:38 How to Negotiate a Sales Deal 22:08 Hiring Mistakes 28:35 Sales Rep Onboarding 33:49 How to Convert on Sales 38:30 Has consumer psychology changed? 43:26 How to Do Weekly Reviews 55:07 Quick Fire Round _______________________________________________ Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Frank Fillmann on Twitter: https://twitter.com/FillmannSFDC Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact _______________________________________________ #FrankFillman #Salesforce #HarryStebbings #SalesLeader #salesrep

Frank FillmannguestHarry Stebbingshost
Mar 21, 20231h 1mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Sales Leader Frank Fillmann Reveals Enterprise Playbooks, Hiring, And Negotiation Secrets

  1. Frank Fillmann, a veteran enterprise sales leader (ex-Salesforce, IBM), breaks down how he thinks about building repeatable, relevant sales playbooks by starting from total addressable market (TAM) and customer outcomes, then working backwards.
  2. He goes deep on hiring and developing sales talent—how to spot high-potential reps, structure teams around complementary profiles (closer, visionary, hunter), and why psychological safety and in-the-trenches coaching matter more than pitting reps against each other.
  3. The conversation covers creating demand that doesn’t yet exist, multi-threading in large accounts, negotiation that starts with customer value instead of price, and adapting to today’s CFO-driven, efficiency-obsessed buying environment.
  4. Fillmann also shares views on forecasting in uncertain markets, aligning comp plans with company metrics, fixing sales–customer success friction, and why empathy and face-to-face relationships are still the non-negotiable core of great sales.

IDEAS WORTH REMEMBERING

5 ideas

Start sales strategy from the money (TAM) and work backwards.

Map opportunities as near vs. far, big vs. small, and known vs. unknown demand; then design your playbook and territory focus so reps are always digging in the right spot instead of discovering real opportunities late in the year.

Make playbooks industry- and persona-specific to compress ramp times.

Translate product features into 4–5 simple slides about the customer’s world (problems, use cases, proof, outcomes, success plan) so new reps can be relevant in weeks instead of quarters, and customers feel understood from the first call.

Hire for potential over experience, then pair high-potentials with proven alphas.

In most cases, Fillmann prefers high-potential reps (except on ultra-high-profile accounts) and accelerates them by placing them on teams with experienced ‘alpha’ closers—while avoiding pairing two alphas together, which creates toxic conflict.

Coach in real time, in the field—not via quarterly post-mortems.

He advocates obsessive preparation, joint customer meetings, and immediate debriefs where leaders first invite critique of their own performance, framing feedback as collective craft improvement rather than top-down evaluation.

Create demand by uncovering latent problems and inventing new budget.

Instead of fighting over existing line-items, great reps discover problems the customer doesn’t yet know how to solve, build a compelling vision, and align a malleable platform to the customer’s long-range goals—similar to how the iPhone created an entirely new category.

WORDS WORTH SAVING

5 quotes

If you can recruit good people and treat them great, by definition they hit their goals, I'm hitting my goals, and the company's happy.

— Frank Fillmann

I always start with the money and work backward, and I focus on TAM… are we digging in the right spot?

— Frank Fillmann

The best teams take three-point shots. It encourages you to take more risks, and the outcome is significantly better than a conservative mindset.

— Frank Fillmann

It's not about you, it's about your team. I want my team to be more successful than I ever have been.

— Frank Fillmann

Hiding information and trying to be protective—that’s 20 years ago. Customers have access to everything now.

— Frank Fillmann

Designing effective, industry-specific sales playbooks and TAM-first strategyHiring, segmenting, and developing different sales rep archetypesCreating demand where none exists and selling to unknown/latent budgetsNegotiation strategy, value framing, and selling to CFOs in this macro environmentOnboarding, coaching, and measuring performance in long enterprise sales cyclesMulti-threading large accounts and aligning internal functions (especially customer success)Compensation design, forecasting, and the evolving nature of sales tactics post-COVID

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