The Barbell Strategy (for Building Pipeline)

How to balance quick wins with big bets

The Barbell Strategy (for Building Pipeline)

Read Time = 3 minutes

It’s Monday morning.

You log into Salesforce.

Coffee in hand, half awake, ready to map your week.

The dashboard flashes:

  • This months pipeline” has shrunk since your last refresh

  • “Response rate” has dipped even as activity volume climbs

  • New opportunities created” has flatlined

You start clicking around.

Stale conversations. Cold accounts. Prospects who ghosted you weeks ago.

The pit in your stomach grows.

You need pipeline.

More importantly, you need wins.

But where the hell do you start?

The Turning Point

Earlier this year I consulted a $30M ARR company to help build an outbound GTM channel.

New to the business and eager to prove my value quickly, I dove in.

What I found wasn’t broken systems or bad people.

It was something more familiar: activity without clarity.

Reps were chasing every half-fit account in sight.

Founders were fielding inbound leads that weren’t ICP.

Partnerships were scattered across conversations that sounded good but went nowhere.

Everyone was busy, but no one was making progress.

The Barbell Strategy

Think about Billy Beane in Moneyball.

He didn’t try to swing for the fences every at-bat.

He built a system where players could consistently get on base — singles and doubles that kept runs coming in.

But he also left room for the occasional big swing — the home run that changes the scoreboard in an instant.

That’s how the barbell works in GTM:

  • On one side: Quick wins → steady, reliable, predictable plays that keep momentum alive. These are your singles and doubles — not flashy, but they build confidence and pipeline.

  • On the other: Strategic bets → longer-term opportunities that could create outsized returns. These are your home run swings — they take longer to develop, but one hit can change the trajectory of your quarter (or year).

  • In the middle: the noise → “meh” opportunities that drain your energy without real payoff. Lazy fly ball to center field — looks good off the bat, but it never lands.

This is a concept Nassim Taleb introduced for investing that can be applied to your pipeline efforts too

How It Works in Real Life

For a Rep organizing a territory

  • Quick wins: Warm inbound leads, existing customer referrals, ICP accounts you know how to close.

  • Strategic bets: Big-name logos, new verticals, outbound sequences that take quarters to mature.

  • Skip the noise: Half-fit accounts and ghosted prospects you keep chasing out of guilt.

For a Founder building GTM

  • Quick wins: Direct outbound to proven personas, reliable referral channels.

  • Strategic bets: Partnerships in emerging ecosystems, experimenting with new distribution models.

  • Skip the noise: Marketing experiments that suck cash without leverage (big event sponsors)

For a GTM Leader

  • Quick wins: Double down on your top-performing reps, your most consistent partners.

  • Strategic bets: Pilot programs with disruptive partners, bold plays into new markets.

  • Skip the noise: Spreading headcount and budget across “okay” initiatives, trying to turn D players to C players

Next week week I gotta find a football analogy. We’re back.

Until then,

TSG

P.S. I reply to all emails.