Outside Sales Manager, Strategic

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.