Sitreps

SaaS

HeadOfSales

$150–160k Philadelphia, Pennsylvania, United States; New York, New York, United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Executive candidates.

The Brief

“Head Of Sales at Sitreps. Skills: Sales motion building, Team management, Revenue generation. Build sales motion. Design commission plans”

What You'll Achieve.

Get business to $5M ARR in 2026; Help establish path to $30M ARR in 2027

Industry & Context.

SaaS
Eligibility Requirements

Travel to Philadelphia 2 days/week

What They're Looking For.

Must Have

7 to 12 years in sales, 3 years leading quota-carrying team, Building or rebuilding sales motion, Software-to-trades experience, Data fluency, Operational execution

Nice to Have

Construction exposure, AEC exposure, Glazing exposure, Curtain wall exposure, Architectural metals exposure, Veteran background, Prior service background, Direct experience hiring AEs, Ramping geographically dispersed AEs, Managing geographically dispersed AEs

What You'll Do.

Design commission plans

Write commission spreadsheet

Translate ethos and pathos

Close enterprise opportunities

Establish path to ARR

How You'll Work.

Team & Collaboration

Partner with founder

Full Job Description

Head of Sales Philadelphia, PA Title evolves to Chief Revenue Officer as the company scales. About the Client The company builds Virtual Bid Assistants for commercial glazing and architectural metals contractors. Their software plus services pulls scope out of RFPs, manages RFIs, and generates proposals so estimators stop missing deadlines and start winning the work they actually want. The business is currently at roughly $2M ARR, targeting $5M by the end of 2026 and $30M by the end of 2027. Backed by leading early-stage investors and headquartered in Philadelphia. About the Role The company has product-market fit, real customers, and an industry-baked-in top of funnel via independent reps. What they don't yet have is a fully built sales motion. The founder is currently the primary closer. The organization is preparing to hire ten Account Executives across the country, each a glazing-industry veteran selling to specialty contractors they've known for decades. The company now needs a leader who can build the system that allows those AEs to succeed at scale. Responsibilities Build the sales motion from scratch. CRM stand-up, sequencing, commission design (including writing the commission spreadsheet yourself), segmentation, ICP, and the closing playbook Manage and coach a national team of 10 industry-veteran AEs. These are not classic SaaS reps. They are people who have been selling to contractors for 25 years and need a leader who respects that and still raises the bar Translate ethos and pathos selling into a repeatable, gap-selling playbook. Train AEs to move from "the client likes you" to "the client buys because we've quantified the gap" Step in to close on the largest enterprise opportunities where industry-veteran AEs may need a more strategic partner across the table. This is not the day job; the day job is building the team and the system Partner with the founder on customer-profile work, segmentation, and territory design Own the number. Get the business fro

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