Head of Sales (Remote, US - EST preferred)

Stadium

100d • $150,000

About The Position

Stadium is a rapidly growing Global Recognition, Swag, and Gifting platform - a true one stop shop. Companies use Stadium to reward employees, deliver swag, and send gifts through a single integrated platform with a truly global solution. From recognition programs and milestone celebrations to on-demand swag and curated gifting, Stadium offers automations and integrations that save time, cut costs, and build stronger workplace cultures. As we continue our rapid growth, Stadium is searching for a Head of Sales. This role is critical in shaping the future of Stadium’s sales organization - designing strategy, building outbound engines, and coaching a high-performing team. You’ll act as both a strategic leader and player-coach: personally co-selling enterprise deals, mentoring managers, improving forecast accuracy, and driving a disciplined sales operating cadence. This role is ideal for an ambitious sales leader who has scaled SaaS organizations through hypergrowth, thrives in a fast-paced environment, and brings both outbound DNA and enterprise sales credibility. You’ll join a collaborative team with the opportunity to make a direct impact. While this is a remote position, Stadium is based in New York City and the ideal candidate would be based in the US (ideally on the east coast but open to discuss) and able to start with us in January 2026.

Requirements

• 10+ years of B2B SaaS sales experience with 5+ years in leadership roles scaling teams.
• Experience scaling a B2B SaaS company to $100M+ ARR.
• Able to execute rapidly and evolve.
• Enterprise credibility: personally closed complex 6–7 figure deals at 1000+ employee companies.
• Proven ability to build and/or run outbound SDR + AE motions.
• Player-coach mindset: develops entire team and implements behavior change by showing how it’s done.
• Adaptable and low-ego: brings playbooks but tunes them to Stadium’s unique model.
• Strong customer focus and executive presence, with the ability to engage at the C-level.
• Collaborative, approachable, and humble — driven to win, but always team-first.
• Great listener and keen to understanding customer situations and goals before responding with strategic guidance.

Responsibilities

• Own new-business revenue, design the GTM strategy across SMB, Mid-Market, and Enterprise.
• Personally co-sell and close enterprise deals to learn on the ground and build a repeatable playbook for the team.
• Coach and develop AE and SDR Sales Managers to establish a culture of accountability and continuous improvement.
• Scale outbound to become a larger share of sourced pipeline building outbound motions (persona mapping, talk-tracks, QA checklists and pipeline ladders).
• Set up capacity & coverage models (ramp, quota/rep, productivity), refine AE pipeline stages and forecasting.
• Implement consistent AE team frameworks (1:1s, deal reviews, forecast inspections) and prepare board-ready reports.

Benefits

• Opportunity to directly shape Stadium’s journey as it enters a high growth phase.
• Remote work environment.
• Collaborative company culture focused on recognizing and leveraging individual strengths.
• Competitive salary, generous PTO, 401K with match, medical benefits (US only).

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 101-250 employees