Director, Territory Sales

Responsibilities

• Owning revenue: you are directly accountable for hitting ambitious territory sales targets across Boston, Washington D.C., Chicago, and the Great Lakes region
• Building and executing market-specific growth strategies for each territory, tailoring approach to local dynamics, competitive landscape, and customer segments
• Maintaining clear pipelines, holding regular 1:1s, co-selling alongside team members, conducting deal reviews, and being deeply engaged in the day-to-day activity of your team
• Leading, mentoring and developing Territory Managers to hit and exceed their individual quotas; identifying strengths, closing skill gaps, and helping each rep grow into their territory
• Spending meaningful time in market, this role requires up to 50% travel to be present with your team and key customers across all territories
• Overseeing and collaborating with business development resources embedded in or supporting territories, including managing through a BD team manager as the team scales
• Contributing to and improving our sales processes, playbooks, and tools — identifying what’s working across territories and scaling best practices
• Working with partnerships, marketing, product, and leadership on go-to-market strategy, brand presence in key cities, and new market expansion planning
• Build strong relationships with property managers, co‑op boards, and other key stakeholders, ensuring Runwise is viewed as a reliable and valued partner
• Foster a culture of internal mobility by developing and promoting top performers, while maintaining healthy candidate pipelines to support future growth
• Lead and manage a team of Territory Managers with rigor, accountability, and consistency, while creating an environment where talented people want to stay, grow, and deliver their best work

Requirements

You have 7+ years of B2B sales experience, including at least 3 years directly managing a team of quota-carrying Account Executives, Territory Managers, or equivalent roles — with a track record of hitting or exceeding team revenue targets

Qualifications

• You thrive in fast-paced, high-growth startup environments where the playbook is still being written and you’re expected to figure things out quickly
• You are a hands-on manager — you don’t manage from a distance; you inspect pipelines, join calls, ride-along on deals, and are deeply engaged with your team’s day-to-day
• You are highly analytical and data-driven: you use CRM data and pipeline metrics to understand what’s working, identify gaps, and make decisions (Salesforce experience strongly preferred)
• You have excellent communication, coaching, and relationship-building skills both with your team and with key customers
• You are comfortable with ambiguity and take ownership — if something isn’t working, you diagnose it and fix it
• You see this as a leadership platform, not just a number to hit. You want to build something, grow people, and take on more scope over time.

Benefits

• Medical, dental, and vision insurance
• HSA & FSA options
• Paid Parental Leave
• Access to Talkspace & Health Advocate
• Flexible PTO
• Commuter Benefits
• 401K
• Company paid life insurance
• Voluntary supplemental life insurance
• Free in-office lunch on Wednesdays
• Hybrid work environment
• Summer Fridays
• Monthly L&D Series
• Employee Resource Groups (e.g. DEIB Committee, Run Club)