As a Strategic Outside Sales Manager, you will lead a team of Territory Managers focused on high-velocity acquisition of independent restaurants. This role is ideal for a hands-on leader who has personally sold in SMB, understands volume-driven sales motions, and has consistently delivered results as a people manager. You will be a player/coach expected to sell SMB and Mid Market sized deals in order to ensure continuous alignment and understanding of the challenges sellers face on a daily basis.
You’ll be responsible for driving predictable revenue, strategic initiatives—including building strategy on how to develop the region through strategic sales and strategic referral partners—developing top talent, and reinforcing a disciplined outside sales motion and metrics-driven sales culture.
This role reports directly to the Director of Sales and will manage a team of ~10 Territory Managers. Requires travel in markets located in South & Central Florida, Chicago, Virginia & West Virginia, Washington, California, Kentucky & North Carolina at least 2 times a month.
Specifically, you will:
- Lead, coach, and develop a team of SMB Territory Managers in a high-velocity sales environment
- Drive consistent performance against weekly, monthly, and quarterly revenue target
- Travel to Territory Managers at least 2 times a month to drive productivity through in-person coaching and co-selling
- Run effective 1:1s, pipeline reviews, forecast calls, and live call coaching
- Maintain accurate forecasting within ±15% variance through disciplined pipeline management
- Partner closely with Sales Enablement to identify skill gaps and deliver targeted training
- Collaborate with Revenue Operations on process optimization, tooling, and reporting
- Hire, onboard, and ramp top-performing sales talent
- Ensure strong Salesforce hygiene and data integrity to maximize conversion and productivity
- Build and sustain a high-performance, high-accountability team culture
- Dive in personally as a player/coach to help support your team and close deals individually
Within 30 Days You’ll:
- Progress through our Ramp Camp (ChowNow’s New Hire Onboarding Experience)
- Shadow in-person selling and sales calls
- Cross-train with Onboarding, Customer Success, and Support to understand the full customer lifecycle
- Launch weekly 1:1s and establish individual development plans
- Build and customize Salesforce dashboards for pipeline visibility, conversion, and rep productivity
- Begin weekly reporting cadence on attainment, conversion rates, and pacing
Within 60 Days You’ll:
- Complete a full team assessment and deliver targeted coaching plans both virtually and in-person
- Partner with Enablement to launch training focused on highest-impact performance gaps
- Meet with multiple restaurant partners to deepen understanding of buying triggers and competitive positioning
- Publish your first playbook updates based on real deal data and customer insights
Within 90 Days You’ll:
- Implement at least one process or tooling improvement with Revenue Ops
- Establish an ongoing Territory Manager hiring pipeline in partnership with Recruiting
- Operationalize playbook governance—win/loss reviews, talk track iteration, and adoption accountability
- Drive measurable improvements in data integrity, conversion rates, and forecast accuracy
- Build a strong, engaged, execution-focused team culture
- Start making 5-10 discovery calls a month in order to work toward your first close
You Should Apply If You Have:
- 4+ years of Strategic sales management experience in SMB, high-velocity SaaS or marketplace environments
- Demonstrated experience in strategic sales
- Demonstrated experience in both inside and outside sales
- A proven track record of consistently hitting or exceeding quota as a manager
- Prior experience selling SMB yourself—you understand the motion, objections, and pace
- Demonstrated success improving conversion rates, ramp times, and rep productivity through both virtual and in-person coaching
- Strong coaching instincts with a people-first leadership style
- Deep comfort with Salesforce, forecasting, pipeline analysis, and performance metrics
- The ability to balance strategy and execution—you can build the plan and jump in to close when needed
About Our Benefits:
- Estimated On Target Earnings (OTE): $130,00-$165,000 (depending on candidate experience and location)
- Ongoing training and growth opportunities.
- A "Best Place to Work" winner multiple times where we focus on creating a great employee experience.
- Rock solid medical, dental, and vision plans.
- Mental Health Coverage - we offer several programs to support your mental health and wellness goals.
- Unlimited Paid Vacation. We expect you to work hard, but still enjoy your personal life
- 7 weeks of baby bonding time for all new parents (within the first year of birth or adoption), 8 Weeks of Paid Pregnancy Leave.
- 401(k) Matching
- Employer-contributing student loan assistance program or continuing education reimbursement program
- Employee Stock Incentive Plan.
- Pet insurance for your fur babies
- Consistent & fair leadership: we’ll share info, set clear goals, show you respect, and treat everyone fairly.
- Enough freedom to spread your wings while still holding you accountable.
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