Director, Mid-Market Sales

TechnoMile is the leading provider of AI-powered software solutions purpose-built for companies that sell to the government. Trusted by government contractors across industry, TechnoMile helps GovCon teams manage the full lifecycle of winning and executing federal, state, and local contracts – from opportunity identification through contract management. With AI-driven insights, automated workflows, and deep domain expertise, TechnoMile is redefining how companies navigate the complexity of doing business with government.

About the Role

TechnoMile is seeking a Director, Mid-Market Sales, to join our Sales team. Reporting to the Chief Revenue Officer, you'll own the Mid-Market segment end to end building, coaching, and leading a team of Account Executives and Business Development Representatives who land new logos and expand accounts across the broad mid-sized GovCon market. You'll carry the segment's bookings number, set the sales motion, and build the team and operating rhythm that make it repeatable.

We believe this role is perfect for a player-coach who has scaled a mid-market SaaS sales team, is energized by a large and underpenetrated market, and wants real ownership of a segment's strategy, hiring, and results. As part of a company that's building AI-enabled products, we're looking for someone who is comfortable using AI tools to enhance their own work and their team's performance. You'll be part of a culture that values experimentation, continuous learning, and finding smarter ways to win.

This role is open to candidates located in the Washington, DC metro area, and is hybrid role reporting to our Tysons Corner, VA office, typically 2-3 days onsite, or otherwise determined by leader and team.

About the Team

Our field Sales team is a fast-growing, quota-carrying organization split across Enterprise and Mid-Market segments, all focused on helping GovCon organizations run compliant, efficient revenue operations. The Mid-Market team, made up of Account Executives and Business Development Representatives, is responsible for landing new logos and expanding existing accounts across a large and underpenetrated market, working alongside Sales Engineering, Revenue Operations, and Marketing.

What You'll Work On

●      Own the Mid-Market bookings number: Be accountable for segment new-business and expansion targets, with accurate weekly and quarterly forecasts delivered to the CRO and Director of Revenue Operations.

●      Build and lead the team: Recruit, onboard, coach, and develop a high-performing group of Mid-Market Account Executives and BDRs, setting clear goals and creating accountability and a low-ego, winning culture.

●      Design the Mid-Market sales motion: Define ideal customer profile, segmentation, territory and account coverage, qualification criteria, and stage definitions, balancing inbound and self-sourced outbound pipeline.

●      Drive pipeline generation: Partner with Marketing and Revenue Operations on campaigns, events, and account-based programs, and hold the team to pipeline coverage targets (typically 3-4x quota).

●      Run a disciplined operating cadence: Lead pipeline reviews, deal inspection, forecast calls, and QBRs using Salesforce and Gong, applying a formal methodology (e.g., MEDDIC) consistently.

●      Coach on the deal: Join key calls and negotiations, help reps navigate multi-stakeholder buying groups, and step in to close strategic opportunities.

●      Partner cross-functionally: Work closely with Sales Engineering, Product, Professional Services, and Customer Success to ensure strong technical wins and clean transitions after the sale.

●      Shape GTM planning: Contribute to capacity, quota, territory, and compensation planning with the CRO and Revenue Operations, and provide market feedback to Product and Marketing.

●      Represent TechnoMile: Build relationships with GovCon customers, partners, and industry groups, and show up at key events.

●      Leverage AI and automation tools to sharpen prospecting, account research, coaching, call review, and forecasting, and identify opportunities to embed AI into your team's workflows.

What We're Looking For

●      Experience: 8+ years of B2B SaaS sales experience, including 3+ years leading quota-carrying sales teams (ideally Mid-Market or commercial segments) with a consistent record of exceeding targets.

●      Team building: Demonstrated success hiring, ramping, coaching, and, when needed, transitioning AEs and BDRs, and building a team culture that retains top talent.

●      Segment ownership: Experience owning a segment bookings number, including forecasting, pipeline management, and territory and quota design.

●      Methodology: Trained in and committed to a formal sales methodology (e.g., MEDDIC, Sandler, Strategic Selling, or Solution Selling), with the discipline to inspect deals and coach to it.

●      Complex sales: Experience selling business applications (e.g., ERP, CRM, CLM, Asset Management) to multiple stakeholders and executive buyers in cycles typically ranging from 3-6 months.

●      Executive presence: Ability to communicate clearly and credibly with the CRO, CFO, customers, and partners, and to operate as a collaborative peer across functions.

●      Approach: A hungry, entrepreneurial, and hands-on approach; you're comfortable building process in a fast-growing environment.

●      AI fluency: Hands-on experience using generative AI and automation tools to boost productivity, with sound judgment on when to lean on AI versus human insight.

Preferred Qualifications

●      Experience selling into government contractors, aerospace and defense, or other regulated or federal-adjacent markets, and familiarity with the federal buying process and language.

●      Experience selling GovCon ERP, CRM, CLM, or proposal/capture management solutions.

●      Experience building outbound BDR/SDR programs and a clear path from BDR to AE.

●      Experience in a growth-stage SaaS company scaling a team from a small base.

Our Tech Stack

You'll work with technologies like: Salesforce, Gong, and standard SaaS pipeline and forecasting tools.

Will You Thrive at TechnoMile?

At TechnoMile, we come from many backgrounds, but we're united by our core values and our drive to pursue greater opportunity. Together, we achieve the extraordinary, turning the improbable into possible.

●      Stronger Together: We know it takes people with different backgrounds, distinct experiences, and unique points of view to make our company succeed. We treat one another with trust and respect and work together, knowing we win or lose as a team. We take time to have fun together, share our appreciation for one another, and celebrate achievements.

●      Relentless Customer Focus: Taking care of our clients is our first priority and at the core of everything we do. We listen to our customers and seek to exceed their expectations. We keep our promises, and we acknowledge and learn from mistakes when we make them.

●      Humble, Hungry, and Smart: We are curious and seek to continuously learn. We avoid arrogance, recognizing that our clients, co-workers, and partners bring knowledge and experience that help us achieve our shared goals. We think creatively, devise new approaches to solve problems, and seek to deliver solutions and insights that others cannot.

●      Aim High: We are committed to the highest standards of ethical conduct in all that we do, and we take pride in providing high quality products and services that we stand behind.

Why You'll Love Working at TechnoMile

At TechnoMile, we're passionate about creating an environment where you can succeed, both personally and professionally. Here's what you can look forward to:

●      Work-life Integration: Unlimited PTO, because we trust you to manage your time and get your work done.

●      Competitive Benefits: A 401(k) match, plus health coverage with employer-paid or employer-contributed HSA options.

●      Growth & Development: An annual professional development allowance to support your learning and growth.

●      Where You'll Work: A mix of hybrid and remote roles, with the setup determined by team and position.