Required Skills & Experience
Qualifications
- 7+ years of B2B SaaS or enterprise technology sales experience, including 1–3 years in a team lead or manager role
- Demonstrated track record of exceeding quota as both an individual contributor and a people manager
- Deep familiarity with SaaS sales metrics: ARR, CAC, LTV, NRR, pipeline coverage, and sales cycle velocity
- Hands-on CRM proficiency (Hubspot preferred); experience with sales engagement tools (Outreach, Salesloft, etc.)
- Strong enterprise selling skills including multi-threading, executive engagement, and value-based selling
- Excellent coaching, communication, and organizational skills
- Comfortable operating in early-stage, high-growth environments where process is still being builtFleet management, transportation, logistics, telematics, maintenance, asset management or related industry experience is beneficial but not required.
Bachelor's degree requiredSuccess Metrics
Job Description
Position Summary The Sales Manager – Digital Fleet is a player-coach responsible for helping build and scale the new customer acquisition motion for Digital Fleet.. Reporting directly to the VP of Sales, this role will initially operate as both an experienced individual contributor and emerging sales leader, personally developing and closing new business while helping establish the processes, behaviors and operating discipline that will support a growing sales team.. The Sales Manager translates the revenue strategy set by the CRO into day-to day sales execution - owning outbound prospecting, enterprise demos, pipeline development, and deal closure within their team and book of business. As an early member of the Digital Fleet sales organization, this leader must be a hands-on builder who can recruit, onboard, and develop Sales Representatives while simultaneously closing business. This role is expected to grow in scope as the sales organization scales from 4 to 6 direct reports under the VP of Sales over the first two years. The Sales Manager collaborates closely with Marketing, Customer Experience, and Product to ensure sales motions are tightly aligned with go-to-market strategy and customer needs. This is not a traditional frontline management role on day one. The successful candidate must be equally comfortable opening a new account, leading executive discovery, developing a business case and negotiating a complex SaaS agreement as they are coaching another seller through those activities. The Sales Manager will also play an important role in turning what we learn from early customers into a disciplined and repeatable sales motion. This requires a leader who combines strong enterprise SaaS selling experience with sound judgment, curiosity, accountability and a willingness to remain close to customers and deals. Major Responsibilities Team Leadership & Coaching
- Lead, coach, and develop a team of 2–4 Enterprise Account Executives, providing weekly pipeline reviews, deal coaching, and structured performance feedback
- Recruit and onboard new Account Executives as the team scales per the VP's organizational growth plan
- Establish team sales processes, cadences, and accountability rhythms aligned with the VP's operating model
- Model high-performance selling behaviors and a hunter mentality within the team
- Create an environment where sellers openly discuss deal risk, losses and lessons learned so the organization improves quickly.
- Gradually transition personal account responsibilities as management scope increases while remaining actively involved in strategic opportunities when appropriate.
Pipeline Development & Revenue Execution
- Personally own a named account or territory quota while managing team performance to collective targets
- Own complex SaaS opportunities from initial prospecting and discovery through evaluation, business case development, commercial negotiation and contract execution.
- Lead outbound prospecting strategy across target segments, including enterprise fleet and logistics customers
- Guide team through full-cycle SaaS deals: discovery, demo, proposal, negotiation, and close
- Maintain pipeline hygiene and forecast accuracy within HubSpotwith discipline and rigor
- Lead pricing, packaging and commercial negotiations while maintaining appropriate deal economics.
- Model the selling behaviors and discipline expected of future members of the Digital Fleet sales organization.
GTM & Cross-Functional Collaboration
- Partner with the VP of Sales to translate Digital Fleet's go-to-market strategy into a practical, repeatable sales motion.
- Help refine qualification criteria, discovery practices, messaging, competitive positioning, opportunity management and deal strategy based on real customer engagement.
- Establish practical sales processes that create discipline without adding unnecessary complexity.
- Capture and communicate patterns across customer conversations, wins and losses to improve ICP definition, positioning and sales execution.
- Align team selling motions with Marketing campaigns, product positioning, and Customer Experience handoffs
- Surface market intelligence, competitive insights, and customer feedback to the VPof Sales, Marketing and Product leadership
- Coordinate with the Customer Experience team to ensure seamless transitions from closed-won to onboarding and adoption Forecasting & Reporting
- Deliver accurate weekly and monthly forecasts to the VP of Sales using defined SaaS metrics
- Track and report on team quota attainment, win rates, deal velocity, and pipeline coverage
- Identify performance gaps and implement corrective action plans for underperforming reps