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.
Skills Required
- 4+ years of strategic sales management experience in SMB, high-velocity SaaS or marketplace environments
- Demonstrated experience in strategic sales
- Experience in both inside and outside sales
- Proven track record of consistently hitting or exceeding quota as a manager
- Prior experience selling SMB directly
- Demonstrated success improving conversion rates, ramp times, and rep productivity through virtual and in-person coaching
- Strong coaching instincts with a people-first leadership style
- Deep comfort with Salesforce, forecasting, pipeline analysis, and performance metrics
- Ability to balance strategy and execution; willing to act as player/coach and close deals personally
- Willingness and ability to travel to specified markets at least twice a month
What the Team is Saying
ChowNow Compensation & Benefits Highlights
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Healthcare Strength — Health coverage includes comprehensive medical plans plus dedicated mental‑health support, with extras like fitness stipends and pet insurance. This combination indicates strong core protection with added wellness options.
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Parental & Family Support — Paid parental and family leave are provided, with baby‑bonding time for all new parents and paid pregnancy leave highlighted. These policies signal meaningful support for caregivers during family milestones.
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Leave & Time Off Breadth — Unlimited paid vacation and paid holidays are part of the package. This breadth can enable substantial time away when supported by team norms.
ChowNow Insights
What We Do
ChowNow’s vision is to become the leading North American platform connecting diners and independent restaurants for at-home dining. The ChowNow Platform continues to grow its product offerings and bring restaurants and diners closer together. Our marketplace provides commission-free ordering for restaurants nationwide and diners with an ever-growing selection of independent restaurants. Our demand network provides diners with the ability to order where they’re already online, including Google, Yelp, Instagram, Snap, and many others. And our white-labeled online ordering system provides restaurants with a branded experience for diners on their website and their own iOS and Android apps for a reasonable monthly fee regardless of order volume. To date, we’ve created over 20,000 apps for our restaurant partners – something that’s never been done before in our category. We operate this way because of our belief in being fair, sustainable, and equitable with our restaurant partners and the same goes for our culture.
Why Work With Us
Diversity, teamwork, and mutual respect are among our core company values. We pride ourselves on giving our teams plenty of opportunities to make their mark. Join us and help ensure ChowNow becomes the diner’s first choice for socially responsible online ordering. Together we can preserve neighborhood flavor, one restaurant at a time.
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ChowNow Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
Our hybrid policy asks local Los Angeles employees to come in 2 times a week to allow for in person collaboration and cross-functional relationship building. Our open air, Culver City Headquarters is spacious and inviting for teams to be together.
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