Head of sales with 14 years in B2B software sales, leading teams at growth-stage companies. Built a 45-person sales organization that grew new ARR from $8M to $27M a year. Owns hiring, sales process, forecasting and compensation, and works closely with marketing and customer success on the full revenue engine.
Experience
Head of Sales, Shelfwise Retail Tech (Chicago, IL)
Jan 2022 – Present
Lead 45 people across SDR, mid-market and enterprise teams, growing new ARR from $8M to $27M a year
Hired 6 sales managers and built a MEDDICC-based process that lifted win rate from 19% to 26%
Own the bookings forecast to the board, landing within 4% for 8 straight quarters
Redesigned compensation with finance to balance new logos and expansion
Director of Sales, Arcline Commerce (Chicago, IL)
Apr 2017 – Dec 2021
Built the mid-market team from 5 to 18 reps, exceeding plan 4 of 5 years
Launched the first enterprise motion, closing 3 deals over $500k
Hired 18 reps across 2 regions
Account Executive, Keelpoint Software (Evanston, IL)
Jun 2012 – Mar 2017
Ranked top 10% of reps for 4 years, selling to retail and CPG buyers
Earned President's Club 4 times
Education
BBA, Marketing, University of Notre Dame (Aug 2008 – May 2012)
Sales: Process design, forecasting, enterprise selling, compensation planning
Methods: MEDDICC, Challenger, Force Management
Tools: Salesforce, Clari, Gong, Outreach
How to write a Head of Sales resume
A strong Head of Sales resume shows quota attainment, deal size, and the customer outcomes you delivered. Show the organization you ran (team size, budget, revenue) and the business results you are accountable for.
Sections, in order
Summary
Experience
Skills
Education
Length: Two pages are common for leadership roles; keep the first page strong enough to stand alone.
Summary: Lead with your leadership scope and the business outcomes you are known for.
Skills to feature
Prospecting
Discovery and qualification
Negotiation
Pipeline management
CRM (Salesforce, HubSpot)
Account management
Customer onboarding
Renewals and expansion
Product demos
Customer empathy
Example bullet points
Closed $2.4M in new ARR in FY24, reaching 132% of quota and ranking #2 of 18 reps
Built an outbound sequence for mid-market accounts that booked 60 qualified meetings a quarter
Raised CSAT from 86% to 94% by introducing tiered routing and a 24-hour follow-up standard
Tips from recruiters
Put quota attainment and ranking in the first bullet of every sales role.
State deal size and sales cycle so readers understand the segment you sell into.
For support roles, show volume handled alongside quality metrics such as CSAT.
Recommended templates
Modern (ATS-friendly): Clean single column with accent headings and rules
Classic (ATS-friendly): Jake's-style LaTeX classic: small caps and hairline rules
Ledger (ATS-friendly): moderncv banking: accent name, bold dates on the right
Head of Sales resume FAQ
What should a Head of Sales resume include?
A Head of Sales resume should show quota attainment, deal size, and the customer outcomes you delivered. Use these sections in this order: Summary, Experience, Skills and Education. Show the organization you ran (team size, budget, revenue) and the business results you are accountable for.
What is the best resume template for a Head of Sales?
Modern, Classic and Ledger work well for Head of Sales roles. They are single-column with standard headings, so applicant tracking systems (ATS) parse them reliably.
How long should a Head of Sales resume be?
Two pages are common for leadership roles; keep the first page strong enough to stand alone.
Which skills should a Head of Sales put on a resume?
Prioritize the skills named in the job posting. Common ones for Head of Sales roles are Prospecting, Discovery and qualification, Negotiation, Pipeline management, CRM (Salesforce, HubSpot) and Account management.
How do I write strong Head of Sales resume bullet points?
Start with an action verb, say what you did, and end with a measurable result such as quota attainment, ARR closed and win rate. For example: "Closed $2.4M in new ARR in FY24, reaching 132% of quota and ranking #2 of 18 reps."