Nick J

Sales leader with 9+ years of experience building and scaling high-performing SaaS sales teams. In the weeds mentality and hands on approach with a proven track record developing account executives through structured coaching, MEDDPICC, Challenger, and Gap Selling methodologies, while improving forecast accuracy, conversion rates, and average deal size. Experienced partnering with Product, Marketing, RevOps, and executive leadership to refine GTM strategy, optimize customer onboarding, and accelerate revenue growth through data-driven experimentation and AI-enabled sales execution.

Sales Manager at Circle (2024-01 – Present)

Manage one sales team with 5 Account Executives selling into the mid market.

• 118% attainment average in 2024, 123% in 2025. On pace for 130% in 2026. Number one performing sales team during entire tenure.
• Rolled out a standardized sales methodology rooted in Gap Selling, Challenger, and MEDDPICC, increasing qualified-to-close conversion by 35% while growing average deal size by 22%
• Partnered with executive leadership to redesign packaging and pricing strategy, increasing Net Revenue Retention by 8% through higher-value expansion opportunities
• Worked with RevOps, Product, and executive leadership to refine ICPs, improve lead routing, and increase expansion revenue through a more targeted GTM motion
• Built AI-powered workflows with Claude MCP to improve call coaching, performance analysis, opportunity prioritization, and seller productivity
• Implemented a repeatable coaching and deal inspection cadence using MEDDPICC, creating consistent qualification standards, stronger forecasting discipline, and more effective pipeline reviews

Senior Sales Manager at CallRail (2021-08 – 2023-12)

Manage two sales teams with 12 Account Executives and 3 SDRs into SMB, Mid Market, and Enterprise accounts.

• Conversion rates: 59% 2023, 50% 2022, 35% 2021
• ARPU: 10% YoY growth in 2022 and 2023
• Team Quota: 101% 2023, 100% 2022, 96% 2021
• Built and implemented a standardized sales playbook centered on Gap Selling, Challenger, and MEDDPICC, creating a repeatable coaching framework across two sales teams
• Established a structured coaching program including call reviews, role plays, deal inspections, and peer coaching that improved execution and ramp time
• A/B testing with Outreach messaging increased completed prospect meetings 38% while decreasing closer workload
• Partnered with Product Marketing to improve in-app onboarding and accelerate trial-to-paid conversion
• Managed forecasting, pipeline inspection, and opportunity reviews across two teams, reinforcing disciplined qualification and accurate commit forecasting

Account Executive Team Lead, Account Executive Team Lead II at CallRail (2020-01 – 2021-07)

Closed complex enterprise SaaS opportunities while coaching three direct reports, partnering closely with Product to improve customer feedback and product-market fit.

• Mentored new account executives on enterprise discovery, stakeholder management, and MEDDPICC qualification while maintaining 138% of quota
• Created a cross-functional "red team" with Product to identify customer adoption risks before launching new products, improving launch readiness and customer experience

Outbound Account Executive, Senior Account Executive at CallRail (2017-12 – 2020-01)

Closed cold scheduled demos with Enterprise level customers and large marketing agency prospects.

• Averaged 154% to plan with an average enterprise deal size of $180K to $200K ARR
• Developed the team's enterprise demo methodology using Gap Selling, Challenger, and MEDDPICC principles, increasing attainment consistency across the sales organization

Outbound SDR at CallRail (2017-06 – 2017-12)

Prospected, cold-called, and scheduled demos for Enterprise level prospects and large marketing agencies.

• Exceeded quota averaging 133% to plan
• First SDR hire; my playbook became the foundation we used to hire and ramp 5 more SDRs and scale the outbound motion

Sales Executive at C.H Robinson (2016-01 – 2017-06)

Prospected, cold-called, and met with prospects in person. Designed and implemented third-party logistic solutions.

• Full cycle closing to SMB and mid market prospects

Varsity Offensive Line Coach at Harrison High School Football (2013-08 – 2015-12)

• Seven linemen in three seasons received college scholarships

Head Varsity Strength Coach/JV Defensemen Coach at Harrison High School Lacrosse (2014-12 – 2015-12)

• Program helped varsity team reach the state playoff semi-finals

Custom Framer/Cashier at Hobby Lobby Stores, Inc. (2011-05 – 2013-08)

• Led the frame shop in upsell by developing a sales process

Bachelor of Science in Exercise Science – Kennesaw State University (2015-12)

Leadership experience – United States Air Force Academy (2009-07 – 2010-12)