Head Of Sales

Sitreps•Philadelphia, PA

19h•$150,000 - $160,000•Hybrid

About The Position

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. 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.

Requirements

7 to 12 years in sales, with at least three years leading a quota-carrying team
A track record of building or rebuilding the sales motion at an early- to growth-stage company — not just optimizing one that already worked
Software-to-trades experience. You've sold SaaS into blue-collar buyers (specialty contractors, home services, pest control, alarm, construction-tech, field-service). You understand that selling to a glazing GC president is not the same as selling to a CIO
Strong data fluency paired with operational execution. You don't write decks; you write commission plans, dashboards, and call scripts
The type of executive presence that earns respect from a 30-year industry veteran on day one
Comfortable in a founder-led, in-person, build-it-yourself environment

Nice To Haves

Construction, AEC, glazing, curtain wall, or architectural metals exposure
Veteran or prior service background
Direct experience hiring, ramping, and managing geographically dispersed AEs

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 from ~$2M ARR to $5M in 2026 and help establish the path to $30M in 2027
Report directly to the CEO
Grow into a CRO-level leadership role as the company scales