Why Hiring a Great VP of Sales Takes 12-18 Months
The hidden timeline challenges in recruiting top sales executives for SaaS companies
1The VP Sales hiring paradox
Even with perfect hiring processes, SaaS companies struggle to land great VP Sales candidates. At $6M ARR with 100% growth, companies assume they're attractive, but top candidates still hesitate. The issue isn't quality - it's timing and risk assessment from the candidate's perspective. Successful VPs weigh stable high earnings against startup uncertainty, making them deliberate movers. This creates a mismatch between company urgency and candidate caution.
2Why top candidates delay
High-performing VP Sales have little incentive to jump quickly. They typically enjoy strong cash compensation, fair equity, functional teams, and mastered processes. Unlike engineering leaders who may seek technical challenges, sales executives face complete environment changes. Moving means abandoning predictable earnings for unproven territories and new team dynamics. The risk/reward calculation favors waiting for multiple proof points before transitioning.
3The cash vs equity dynamic
While engineers often prioritize equity, VP Sales candidates weigh cash compensation heavily. Their current roles usually provide substantial guaranteed income that startups can't immediately match. Even with exciting equity packages, the immediate income drop creates friction. This financial reality forces candidates to extensively vet opportunities, often requiring 12+ months to observe company traction, product-market fit, and leadership stability before committing.
4Relationship building timeline
The successful hire of LinkedIn's Brendon Cassidy illustrates the extended courtship period. Initial contact as a reference call led to 20 months of relationship building before joining. During this period, the company demonstrated growth, the CEO established trust, and the candidate observed proof points. This extended timeline isn't unusual - top performers want to see sustained progress before leaving secure positions, requiring early cultivation.
5The reference call strategy
Reference checks for other candidates often surface ideal future hires. When seeking references, CEOs should note particularly insightful sales leaders who understand their space. These individuals may become prime candidates later. The reference context allows natural relationship building without immediate pressure to hire. Over time, these connections can mature into hiring opportunities as both parties' situations evolve.
6Why early outreach matters
Companies should begin VP Sales recruitment at $1M ARR, not waiting until urgent need arises. Early outreach allows time for candidates to observe company growth trajectories. Many top performers require 12-18 months to complete their due diligence on market position, product strength, and leadership team. Starting early creates a pipeline of relationships that can convert when candidates feel timing is right, avoiding rushed hires.
7The continuous hiring approach
Smart companies maintain ongoing VP Sales candidate relationships regardless of immediate need. This constant networking surfaces potential fits early and allows natural timing alignment. When the right candidate emerges, companies with established connections can move quickly when the candidate becomes receptive. This contrasts with reactive hiring that forces compromises due to time pressure and limited candidate pools.
8Reframing the hiring mindset
Companies must shift from viewing VP Sales hiring as an event to treating it as a continuous process. The 12-18 month timeline isn't a failure - it's the reality of recruiting proven performers from secure positions. By building relationships early and allowing candidates extended evaluation periods, companies increase chances of landing ideal matches. This patience prevents costly mis-hires while ensuring candidates join when properly motivated.
Original article: SaaStr — Why Hiring a Great VP of Sales Takes 12-18 Months