Director, Mid-Market Sales

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.

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.

• 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

• 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