[Hiring] Outside Sales Manager, Strategic @ChowNow

Role Description

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.

• Drive predictable revenue and strategic initiatives.
• Develop top talent and reinforce a disciplined outside sales motion.
• Manage a team of ~10 Territory Managers.
• Travel in markets located in South & Central Florida, Chicago, Virginia & West Virginia, Washington, California, Kentucky & North Carolina at least 2 times a month.

This is a remote role based in the United States.

Qualifications

• 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.
• Demonstrated success improving conversion rates, ramp times, and rep productivity.
• 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.

Requirements

• 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 targets.
• Travel to Territory Managers at least 2 times a month.
• 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.
• 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.

Benefits

• Estimated On Target Earnings (OTE): $130,000-$165,000 (depending on candidate experience and location).
• Ongoing training and growth opportunities.
• A "Best Place to Work" winner multiple times.
• Rock solid medical, dental, and vision plans.
• Mental Health Coverage.
• Unlimited Paid Vacation.
• 7 weeks of baby bonding time for all new parents.
• 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.