After sifting through over 100 of my meetings with prospect companies, Granola rolled up 7 common concerns. These same frustrations echoed across industries, company sizes, and growth stages. Whether it’s a bootstrapped SaaS startup or a PE-backed services firm, revenue leaders are wrestling with remarkably similar challenges.
Here’s what keeps them up at night…and what they’re really saying when they think no one’s listening or able to tactically solve.
“Our Pipeline Looks Great on Paper, But…”
“We’re booking 40 meetings a month, but half don’t show up and most aren’t qualified.”
This is the #1 complaint I hear. Revenue teams are hitting activity metrics: calls made, emails sent, LinkedIn connections, but the quality is abysmal. They’re celebrating vanity metrics while their actual conversion rates are embarrassing.
The root cause? Most teams are interrupting prospects at the awareness stage instead of catching them at consideration. They’re calling people who just heard about their problem yesterday, not prospects who’ve been researching solutions for months.
The reality check: 73% of the buyer’s journey happens before first contact. If your SDRs are making 200 dials to book 3 meetings, you’re fishing in the wrong pond.
“We Have All These Tools, But They Don’t Talk”
“We’ve got HubSpot, ZoomInfo, Outreach, and five other platforms. None of them integrate properly, muchless enabled us to do more pipeline.”
The modern revenue stack has become a Frankenstein monster. Marketing uses one tool, sales uses another, and ops tries to duct-tape them together with Zapier workflows that break every other Tuesday.
I recently met with a $3M company paying $4,300/month for HubSpot Marketing Enterprise because they had lost control of their marketing tier. Their marketing team couldn’t even tell which campaigns were driving revenue because the data lived all over the place, yet it’s one of the highest expenditures of their organization. In what world…
The wake-up call: Complexity is the enemy of execution. If your team needs a PhD in martech to run a campaign, you’ve already lost.
“I’m the Bottleneck and I Know It”
“Every deal has to go through me. I can’t scale myself.”
Founder-led sales works until it doesn’t. These leaders built their companies on relationships and deep product knowledge, but now they’re drowning in discovery calls while strategic initiatives collect dust.
The irony? They know they need systems and processes, but they’re too busy selling to build them. It’s the classic “too busy chopping wood to sharpen the axe” scenario.
The hard truth: Your company will hit a ceiling equal to your personal capacity unless you build scalable systems that work without you. The executive influence still plays a massive part in the sales productivity, but it’s not running and gunning pipeline anymore.
“Show Me the ROI or I’m Out”
“We tried a fractional CMO last year. Spent $180k and got absolutely nothing to show for it.”
Revenue leaders have been burned. They’ve invested in marketing agencies that delivered beautiful campaigns with zero pipeline impact. They’ve hired expensive consultants who restructured everything (mostly in spreadsheets and docs) except the revenue number.
The new standard: If you can’t tie marketing spend directly to closed revenue within 90 days, you don’t get to stay in the game. Get outta the way.
“Our Website is Pretty, But It Doesn’t Convert”
“We get 1,000 visitors a month and maybe 2 form submissions.”
Companies are spending $50k on website redesigns that look gorgeous but generate zero leads. They’re optimizing for awards, not revenue.
The missing piece? They have no system for capturing buyer intent. Someone visits their pricing page three times in a week, downloads two white papers, and forwards an email to their team – but there’s no mechanism to flag this as a hot lead. The magic is in the small digital tweaks that optimize conversions…followed by a strong, always-on follow up process.
The missed opportunity: Your website should be an intent data goldmine, not a digital brochure.
“Our Database is a Graveyard”
“We have 50,000 contacts, but most are dead emails from 2019.”
Legacy databases are haunting revenue teams. They’re sitting on thousands of contacts they can’t reach because email addresses are outdated, job titles have changed, or people switched companies.
Meanwhile, they’re spending $40k/year on ZoomInfo while using 10% of its features because no one knows how to properly segment and target their ideal customer profile.
The reality: A clean database of 5,000 reachable prospects beats a dirty database of 50,000 ghosts every time.
The Underlying Pattern
What’s fascinating is that these aren’t really separate problems, they’re symptoms of the same root issue: Revenue teams are trying to scale 2015 tactics in a 2026 buyer environment.
Prospects are more sophisticated. They’re doing extensive research before engaging with vendors. They’re immune to generic outreach. They expect personalized, relevant experiences from first touch to close.
But most revenue operations are still built for the world where cold calls worked and spray-and-pray email got responses.
The Path Forward
The companies winning today have figured out how to:
- Build always-on nurture systems that catch prospects at every stage
- Use intent data to identify buying signals before competitors
- Create unified systems that give everyone the same view of the customer
- Measure everything that matters and nothing that doesn’t
The bottom line: Revenue responsibility isn’t about working harder—it’s about building systems that work smarter.
The leaders who crack this code will dominate their markets. The ones who don’t will keep having the same frustrated conversations in 2027.