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Director, Mid-Market Sales

KeepTruckin

KeepTruckin

Sales & Business Development
Nashville, TN, USA · Austin, TX, USA
Posted on Jul 4, 2025

Who we are:

Motive empowers the people who run physical operations with tools to make their work safer, more productive, and more profitable. For the first time ever, safety, operations and finance teams can manage their drivers, vehicles, equipment, and fleet related spend in a single system. Combined with industry leading AI, the Motive platform gives you complete visibility and control, and significantly reduces manual workloads by automating and simplifying tasks.

Motive serves more than 100,000 customers – from Fortune 500 enterprises to small businesses – across a wide range of industries, including transportation and logistics, construction, energy, field service, manufacturing, agriculture, food and beverage, retail, and the public sector.

Visit gomotive.com to learn more.

About the Role

We are seeking a high-performing Sales Director with deep SaaS experience to lead a team of Regional Sales Managers within Motive’s Mid-Market segment. This is a critical leadership role in a fast-paced, high-growth environment, ideal for someone passionate about coaching leaders, driving results, and building world-class sales organizations. You'll play a key role in shaping go-to-market strategy and scaling one of Motive’s most dynamic and rapidly growing sales segments.


Mid-Market Sales at Motive

Motive’s Mid-Market division sits between our SMB and Enterprise segments and drives new business with companies that have 50-149 fleet sizes. Mid-Market is a high-velocity, transactional environment with AEs typically having 1–5 years of quota-carrying experience, many of whom have been promoted internally from our SDR/BDR ranks. Sales cycles often involve product trials and require strong collaboration between AEs, Sales Engineers (SEs), and Account Managers supporting existing relationships.

Today, the Mid-Market organization is composed of 8+ RSM teams, with each RSM overseeing 7–10 Account Executives. The team operates on a round-robin model (not territory-based), and success requires excellent team execution, cross-functional collaboration, and leader-led coaching at scale.


What You’ll Do

  • Lead, coach, and develop a team of Regional Sales Managers, empowering them to lead high-performing AE teams

  • Own performance across a large segment, consistently driving your org to meet and exceed monthly and quarterly revenue targets

  • Partner closely with Sales Enablement, Recruiting, Product, Marketing, and RevOps to scale processes, tools, and resources that support sustainable growth

  • Accurately forecast performance, identify risk, and proactively implement strategies to ensure quota attainment across teams

  • Lead hiring and talent development across your region, from RSMs to AEs, with a focus on excellence, diversity, and retention

  • Foster a culture of accountability, continuous improvement, and performance-driven results

  • Translate sales strategy into day-to-day team execution, holding leaders accountable for driving adoption of process, tools, and playbooks

  • Identify gaps and friction in the sales motion; build cross-functional plans to remove blockers and improve conversion


What We’re Looking For

  • 2+ years of experience as a second-line leader or senior frontline leader, managing sales managers and scaling SaaS sales teams

  • Proven ability to hire, coach, and scale both leaders and reps in fast-growth, performance-driven organizations

  • Deep understanding of pipeline management, forecasting, and data-driven decision-making

  • Strong cross-functional collaboration skills - able to influence across Sales, Marketing, Product, and Operations

  • Executive-level communication skills with the ability to report clearly on performance, risks, and strategic priorities

  • Results-focused mindset with a bias for action and ownership

  • Familiarity with Salesforce and modern sales tech stacks (e.g., Gong, Outreach, Clari, etc.)

  • Experience in transportation, logistics, or hardware-enabled SaaS is a plus

  • Bachelor’s Degree required

Creating a diverse and inclusive workplace is one of Motive's core values. We are an equal opportunity employer and welcome people of different backgrounds, experiences, abilities and perspectives.

Please review our Candidate Privacy Notice here .

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The applicant must be authorized to receive and access those commodities and technologies controlled under U.S. Export Administration Regulations. It is Motive's policy to require that employees be authorized to receive access to Motive products and technology.

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