Talent Strategy as the Foundation for Sales Growth with Ryan Cahill

Sep 8
3 min read

The GTM Kickback! #45 – Ryan Cahill

Released: November 1, 2021

The past year has been unlike anything we’ve seen in the world of sales talent. Salaries are up, competition is fierce, and companies are struggling to recruit and retain the talent they need to grow.

On this episode of The GTM Kickback!, I sat down with Ryan Cahill, Managing Director at Winning by Design and seasoned SaaS revenue leader, to talk about how organizations can adapt to the “talent war” and build strategies that support long-term growth.

What’s Driving the Talent War?

Ryan points to a mix of macro and industry-specific factors:

Remote work has leveled the playing field. Companies can no longer rely on geographic “discounts.” A rep in Nashville commands nearly the same pay as one in New York.
Demand has skyrocketed. According to U.S. Bureau of Labor Statistics, job openings rose from 4M ten years ago to 10.4M today. Demand for talent is simply outpacing supply.
Capital and growth pressure. Record VC investment over the last three years means hundreds of companies are scaling GTM teams simultaneously.

The result: longer recruiting cycles, more candidate leverage, and organizations scrambling to adjust pay, quotas, and expectations.

Recruitment Today: From Interviewing to Recruiting

As Ryan and I both noted, the dynamic has flipped. Companies used to interview candidates; today, they must recruit them.

Candidates know their value, have multiple offers, and won’t hesitate to walk away from a process that feels off. That means organizations must:

Treat the process like a sales motion—nurture candidates, show value, and “close” with urgency.
Move faster—what once took 30–45 days now takes 60–75+ days.
Align compensation and expectations with the market—or risk losing talent before an offer.

Why Retention Comes First

Hiring is hard enough. Replacing strong performers is even harder. Ryan emphasized that the first step in talent strategy is protecting the team you already have.

Review compensation now, not next year. If you’re not at the 75th percentile or higher, your people are at risk.
Adjust quotas where needed to keep reps engaged and earning, especially in Q4.
Invest in frontline managers—the sticky relationship that often determines whether reps stay or go.

“Whatever you have to pay to keep them is cheaper than replacing them.”

The End of the “Perfect Hire”

Many companies chased senior, enterprise-ready sellers to shortcut ramp times. But Ryan says that model isn’t sustainable. There simply aren’t enough of those reps to go around.

Instead, companies need to:

Adjust expectations. Accept that most hires will be less experienced than ideal.
Invest in enablement. Upskill new reps to fill the gaps.
Focus job descriptions. Get granular about what kind of sales experience matters—enterprise vs. transactional, ICP familiarity, personas sold to, etc.

Culture and Transparency as Differentiators

In a candidate-driven market, culture isn’t just internal—it’s public. Reps are doing diligence long before a recruiter calls: checking LinkedIn, Glassdoor, RepVue, Slack communities, and back-channeling peers.

Winning companies are proactive with:

Cultural branding: celebrating wins, diversity, and employee stories externally.
Authentic communication in interviews—no grilling sessions, just transparency and respect.
Equipping frontline managers to build strong day-to-day relationships with reps.

Key Takeaways

Ryan left us with clear action items for revenue leaders:

Shore up existing talent first. Retain before you recruit.
Be proactive about hiring. Start earlier than you think, and involve the whole org.
Adjust to reality. Hire for potential and upskill internally—don’t bank on “perfect” candidates.
Get competitive now. Comp and quotas must align with the market immediately.
Sell your culture. Candidates are doing their homework; make sure your external brand reflects what it’s really like inside.

Final Thought

The “talent war” isn’t a temporary storm—it’s the new reality. Sales organizations that treat talent strategy with the same rigor as revenue strategy will be the ones that win.

As Ryan put it: “With 10.4 million open jobs, this is an employee market. If you don’t think so, you’re not paying attention.”