Director, Mid-Market Sales

TechnoMile•McLean, VA

11h•Hybrid

About The Position

TechnoMile is seeking a Director, Mid-Market Sales, to lead its Mid-Market segment. Reporting to the Chief Revenue Officer, this player-coach will own the segment’s bookings target and strategy, build and lead a team of Account Executives and Business Development Representatives, and establish a repeatable sales motion for acquiring new customers and expanding existing accounts across the mid-sized government contractor market. The role includes responsibility for team hiring and development, pipeline generation, forecasting, sales execution, and segment planning. The Director will work closely with Revenue Operations, Marketing, Sales Engineering, Product, Professional Services, and Customer Success, and will represent TechnoMile with customers, partners, and industry groups. The role also involves using AI and automation tools to improve prospecting, research, coaching, call review, and forecasting. The position is open to candidates in the Washington, DC metro area and is hybrid, reporting to TechnoMile’s Tysons Corner, Virginia office, typically 2–3 days onsite or as otherwise determined by the leader and team.

Requirements

At least 8 years of B2B SaaS sales experience, including at least 3 years leading quota-carrying sales teams, ideally in Mid-Market or commercial segments, with a consistent record of exceeding targets.
Demonstrated success hiring, ramping, coaching, and, when needed, transitioning Account Executives and BDRs, and building a team culture that retains top talent.
Experience owning a segment bookings number, including forecasting, pipeline management, and territory and quota design.
Training in and commitment to a formal sales methodology, such as MEDDIC, Sandler, Strategic Selling, or Solution Selling, with discipline in deal inspection and coaching.
Experience selling business applications such as ERP, CRM, CLM, or Asset Management to multiple stakeholders and executive buyers, typically in sales cycles of 3–6 months.
Ability to communicate clearly and credibly with executives, customers, and partners, and collaborate across functions.
Entrepreneurial, hands-on approach and comfort building processes in a fast-growing environment.
Hands-on experience using generative AI and automation tools to improve productivity, with sound judgment about when to rely on AI versus human insight.

Nice To Haves

Experience selling to government contractors, aerospace and defense, or other regulated or federal-adjacent markets, and familiarity with federal buying processes and terminology.
Experience selling GovCon ERP, CRM, CLM, or proposal/capture management solutions.
Experience building outbound BDR/SDR programs and establishing a clear path from BDR to Account Executive.
Experience scaling a team from a small base at a growth-stage SaaS company.

Responsibilities

Own the Mid-Market segment’s new-business and expansion bookings targets, and provide accurate weekly and quarterly forecasts to the CRO and Director of Revenue Operations.
Recruit, onboard, coach, and develop Mid-Market Account Executives and BDRs, establishing clear goals, accountability, and a low-ego, high-performing team culture.
Define the Mid-Market sales motion, including the ideal customer profile, segmentation, territory and account coverage, qualification criteria, and sales stage definitions.
Partner with Marketing and Revenue Operations on campaigns, events, and account-based programs, and manage pipeline coverage targets.
Lead pipeline reviews, deal inspections, forecast calls, and quarterly business reviews using Salesforce and Gong, applying a formal sales methodology consistently.
Coach representatives on deals, join key calls and negotiations, help navigate multi-stakeholder buying groups, and step in to close strategic opportunities.
Partner with Sales Engineering, Product, Professional Services, and Customer Success to support technical wins and effective post-sale transitions.
Contribute to capacity, quota, territory, and compensation planning with the CRO and Revenue Operations, and provide market feedback to Product and Marketing.
Build relationships with GovCon customers, partners, and industry groups, and represent TechnoMile at key events.
Use AI and automation tools to improve prospecting, account research, coaching, call review, and forecasting, and identify opportunities to incorporate AI into team workflows.