Mid-Market Sales Manager, Midwest

Miter • Chicago, IL

2d • $250,000 - $300,000

About The Position

Miter is hiring a Sales Manager to lead and grow its Midwest Mid-Market Sales team. Reporting to the Head of Sales, this hands-on leadership role involves building, coaching, and managing Account Executives who own defined geographic territories, launch markets, acquire new business, and build a strong sales culture. The manager will combine strategic planning with on-the-ground coaching and customer engagement.

The role requires significant overlap with Central working hours and approximately 25% travel, primarily within the team’s Midwest territories. Travel includes field coaching, customer meetings, industry and company events, and site visits. Miter describes the position as field-first and emphasizes local presence and genuine customer relationships.

Miter builds AI-powered software and embedded payment solutions for construction contractors, including systems for HR, finance, and operations. The company reports growth since launching in 2021 and has raised more than $78 million from investors.

Requirements

• At least 2 years of experience hiring, managing, and developing a team of 6 or more quota-carrying Account Executives in a field- or territory-based sales model.
• A record of consistently exceeding team quotas and helping representatives grow, earn promotions, and win, including through competitive, ground-up territory development.
• Direct field sales experience or experience managing field sales teams, including building pipeline from scratch, maintaining a territory presence, and developing local market expertise.
• Strong coaching skills and a commitment to building high-performing, motivated sales teams.
• An entrepreneurial mindset and adaptability in fast-paced, high-growth environments where the playbook is still being developed.
• Strong business judgment and data fluency to inform decisions and drive predictable results.
• Exceptional communication and relationship-building skills with teams, customers, and communities.
• Willingness and ability to travel extensively within the East Coast region; the role is described as field-first.
• Significant overlap with Central working hours.

Nice To Haves

• Experience in construction, payroll, or related industries.
• Salesforce experience.

Responsibilities

• Hire, develop, motivate, and manage 6–8 full-cycle Account Executives, each responsible for a defined geographic territory.
• Coach Account Executives to become trusted advisors in their local markets.
• Participate in the sales process through ride-alongs, joint customer visits, site visits, trade shows, and local partnerships.
• Conduct regular pipeline and deal reviews, analyze performance, and provide ongoing coaching to help the team meet targets and develop professionally.
• Help the team build pipeline in new and existing markets; coach on local prospecting, account prioritization, and long-cycle sales discipline.
• Partner with product, marketing, launch, and customer success teams to support customer experiences and align on business goals.
• Use CRM and other technologies to track metrics, forecast pipelines, and report on team productivity.
• Foster an entrepreneurial, high-energy, collaboratively competitive team culture grounded in local presence and customer relationships.

Benefits

• Competitive salary, commission, and equity packages.
• Medical, dental, FSA, and vision plans.
• Company-matched 401(k) contributions.
• Flexible PTO.
• 16 weeks of paid parental leave for all parents, including adoptive and foster parents.
• Annual educational allowance for external professional development.
• Snacks, coffee, lunch, and commuter benefits for employees working in an office.
• Company-wide and team-specific off-sites.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed