This article comes from the expert panel, ‘Strategies for scaling your revenue engine and fueling growth’, at our 2023 Chief Revenue Officer Summit.


Ever feel like you’re building your revenue engine while flying it?

Leading experts, Benjamin Samuels, Chief Revenue Officer at WeWork and Jim Pattermann, Chief Revenue Officer at Palmetto Technology Group can relate. 

They’ve steered companies through steep climbs, making growth decisions in real-time, so we picked their brains on battle-tested tips for scaling without crashing. 

How do you rapidly expand while ensuring solid foundations? What transforms initially scrappy teams into smooth-sailing enterprises?

Join us as our thought leaders share field wisdom for constructing sturdy yet agile revenue engines primed for altitude. 

From hiring resilient teams to optimizing systems and sustaining cultures, here’s their insider perspective!

  • Thoughtful hiring and team building
  • Leadership principles
  • Structural optimization
  • Process integration
  • Promote psychological safety
  • Priority realignment

1 . Thoughtful hiring and team building

As Benjamin put it, WeWork was “trying to build the rocket as we were flying it.” He explained that while the charismatic CEO attracted droves of applicants, they still aimed to be analytical about each role’s needs.

However, they likely over-indexed on passion and mission-orientation versus competencies like resilience, grit, and real experience. 

Rather than succumb to hiring blind spots, Jim now starts by asking: What problem are we solving for? What strengths fit best?

He admits early on just vaguely needing “somebody really good” without fully defining skill sets torpedoed new hires. 

“It never works out” long haul without rigorously clarifying expectations, outcomes and which “types of people” suit them.

For sales, that meant ultimately differentiating between “hunters and farmers” rather than assuming “everybody can do everything.” Narrow profiles then allow for targeted recruiting and onboarding.

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2 . Leadership principles

Speaking of culture carriers, hiring frontline managers hastily can tempt catastrophe.

As Jim cautions, “If that level person isn’t the right person, it will sink your organization.” Beyond individual performance, managers mold team dynamics and effectiveness.

Benjamin knows firsthand – bringing on mismatched senior leaders with inflated titles at WeWork wreaked havoc internally. Beyond seeming unfair or untenable financially, perceived incompetence in leadership erodes morale across the board.

So slow down hiring managers until you land the right fit. Side benefit? Fewer painful performance conversations down the road.

To avoid manager mis-hires, Jim now convenes “panel interviews” across multiple stakeholders when assessing senior candidates. This well-rounded perspective also minimizes blind spots. 

So enacting balanced vetting processes promotes fairness and fit. According to Jim, they now even incorporate “case study presentations” from candidates on hypothetical strategic situations to pressure test critical thinking.

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3 . Structural optimization

Particularly in RevOps, siloed thinking and disorder can cripple cooperation, consistency and collective intelligence. Build in structures promoting enterprise-wide cohesion.

Benjamin ultimately retooled WeWork’s org design with clearly delineated but interlinked “mandates and responsibilities” guiding teams. 

The aim? More independence balanced with coordination mechanisms to enable handing off accounts and sharing insights seamlessly.

Like a well-oiled sports team, each player fills a particular position with tailored strengths while coordinating to execute plays. 

Similarly, specialized revenue squad members can fluidly hand off accounts and trade insights to collectively drive sales while retaining focus within their function.

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4 . Process integration 

Startups run lean, scrappy, and undocumented for pace and necessity. But process gaps can painfully surface at scale, making lack of structure a liability.

Jim’s firm Palmetto saw entrepreneurial spirit enabling early victories then backfiring as complexities ballooned: “Too much entrepreneurial ability, going rogue...doesn’t necessarily fly long-term.”

The solution? Incrementally instill operational guardrails while giving culture room to breathe, evolve, and retain magic: “Recognize turning points” ripe for a refresh.

You know that saying about designing the plane while flying it? It doesn’t seem to get easier. 

But with the right hires, mindset, and lean processes boosting collective IQ, revenue engines can smoothly ride growth waves instead of getting crushed.

5 . Promote psychological safety

Counterintuitively, cultures allowing transparent failure discussions drive the highest sustainable performance.

Benjamin helped engender this by establishing routines for open performance feedback, both appreciative and constructive. Rather than let issues silently fester, they implemented processes to quickly course correct. 

As he notes, "If someone is not killing it, they're told, so they can pivot."

They also emphasized collectively learning from failures given the impossibility of flawless execution at scale. 

Revenue leaders should adopt similar frameworks for powering through hurdles without finger-pointing.

Psychological safety promotes promptly ID'ing what’s not working so energies pivot towards rallying solutions rather than assigning blame.

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6 . Priority realignment

The most formidable challenges demand a relay team be running in parallel – a nimble innovation squad dreaming up ideas paired with an operational powerhouse turning them into market reality.

In startups, frontline employees wear all these hats out of necessity, making swift decisions yet rarely documenting why, so all this hard-fought knowledge vaporizes. 

In Jim’s case, his firm realized “too much entrepreneurial spirit” ultimately hampers scaling. Yet he avoided over-correcting to the rigid controls that snuff out creativity.

The solution? Judiciously layer in “added discipline and process” for smoother coordination while ensuring culture stays receptive to disruptive thinking.

Rome wasn’t built in a day. But with a resilient mindset, operational backbone and just enough independence baked in, revenue engines can smoothly scale without losing startup magic.

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Final thoughts

Well folks, that wraps our time with revenue experts Benjamin and Jim. 

Hopefully, their battlefront tips give you some next-level insights into how to lead growth without losing the plot operationally.

In closing, remember scaling requires balancing act across factors:

Hire patiently - prioritizing resilience makes teams anti-fragile as complexity increases

Structure smartly - specialized functions still require crosstalk to enable hand-offs

Mind culture closely - preserve psychological safety so people raise red flags faster

Add light structure - guardrails smooth coordination but don't squeeze creativity

Keep an eye on the horizon! Continually reevaluate what employees and customers need next from the organization.

And with that parting bit of inspiration, we'll sign off. Let the revenue growth begin!


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