How to Build a Sales Team from the Ground Up

Hiring, Compensation Models, and Structure with John McCracken

John McCracken, Former SVP of Worldwide Sales at Castlight Health and Jive Software

John McCracken brings more than 18 years of sales leadership experience across high-growth tech firms. He served as the SVP of Worldwide Sales at Castlight Health and Jive Software, and held senior roles at Inovis, American Express, Warrantech, and PC ServiceSource. He also served on the advisory board of iConclude.

What Founders Should Know About Sales Teams

• Hire differently for inside versus outside sales. For inside sales, look for hungry, early-career talent. For outside sales, prioritize experience and a proven track record at high-performing companies.
• Build a team-based org structure in the early stages. Share quotas across reps and emphasize collaborative selling to break into enterprise accounts.
• Use a simple and clear compensation model. McCracken recommends a 50% base and 50 % commission plan for most roles.
• Sales comp accelerators should drive performance. Design them to increase earnings when a rep crosses 100% of quota and again at 125%.
• High-performing salespeople often have an athletic mindset. They embrace competition, handle rejection, and stay focused through highs and lows.
• Address underperformance early. After two missed quarters, assess pipeline viability. If there is no path to recovery, help the rep transition out with dignity.

Building a Sales Org from Early Stage to Scale

What is the right sales org structure?

It depends on your stage. Early companies benefit from a pod-based or collaborative model, where reps share ownership of accounts. As you scale, layers of management and specialized roles like SDRs, AEs, and customer success become more necessary.
McCracken emphasized staying flexible. Do not over-engineer the structure too early, but make sure there is clarity in roles and accountability.

How should compensation evolve?

Start with a simple plan: 50% base and 50% variable. This keeps things understandable for reps and scalable for leadership.
Add accelerators to reward overperformance. Reps from larger companies often expect to earn 8 to 10 % on deals after quota. Use the 125% benchmark as the next unlock tier to reach 10 to 20 % on commission.

Who makes a great sales hire?

Look for people with competitive drive. McCracken mentioned that former athletes are often successful because they have learned to win, lose, and bounce back quickly.

Also important attributes to look for are:

• Strong communication skills
• Curiosity about the product and customer
• Accountability and personal discipline
• A track record of performance in previous roles

Managing Performance on Sales Teams

When should you intervene?

If a rep misses quota two quarters in a row, it is time for a serious conversation. Review their pipeline.

Are deals stuck? Are targets realistic?

If recovery seems unlikely, support them in finding their next role. Avoid surprises and give people time to land elsewhere with respect.

Considering Growth Equity Capital?

Ready to scale your go-to-market motion or hire a world-class sales team?

We would love to connect. Lead Edge Capital partners with founder-led businesses and supports scale through hands-on operating expertise and global executive networks.

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About John McCracken

John McCracken led high-performing sales organizations at Castlight Health, Jive Software, and other major tech firms. His insights on sales team structure, comp planning, and performance management are based on real experience scaling enterprise sales teams from the ground up.

FAQ: Sales Team Structure and Compensation

How do you build a sales team from the ground up?

Start by hiring inside and outside reps with complementary strengths. Create a clear comp plan, shared goals, and early collaboration across the team.

What is the best comp structure for sales reps?

Use a 50 % base and 50 % commission. Add accelerators at 100 % and 125 % of quota to reward top performers.

How do you structure a sales team at an early-stage startup?

Use a team-based or pod model with shared accountability. Avoid unnecessary layers early on and adapt as the team grows.

What makes a good sales hire?

Look for competitive drive, communication skills, and curiosity. Former athletes or candidates with a history of overachievement often perform well.

When should you replace a sales rep?

After two missed quarters and a weak pipeline, evaluate the path forward. If there is no shot at recovery, help them transition professionally.