Senior Manager, Pilot Success

Geotab•Las Vegas, NV

18h•Hybrid

About The Position

Geotab is seeking a Senior Manager, Pilot Success who will define and drive the evolution, execution, and performance of our pilot program framework — serving as the strategic engine behind accelerated revenue growth and improved win rates for our most complex enterprise accounts. This is a critical leadership role at the intersection of people leadership, process innovation, AI-driven efficiency, and executive stakeholder partnership. If you love building high-performing teams, transforming operations through technology, and making a direct impact on revenue outcomes — we would love to hear from you! As a Senior Manager, Pilot Success, your key area of responsibility will be optimizing the end-to-end pilot lifecycle to increase sales velocity and improve win rates, particularly for strategic enterprise accounts where successful pilot implementation is critical to securing long-term partnerships. You will oversee high-performing, cross-functional teams composed of both people leaders and individual contributors, managing departmental activities through a tiered leadership structure that balances strategic mentorship with tactical oversight. You will lead an AI implementation roadmap to automate manual workflows across pilot data analysis, reporting, and hardware provisioning — shifting your team's effort from manual data processing to high-value strategic consulting. You will own the customer journey for the pilot phase, partnering with Product and UX teams to reduce friction and enhance the experience for both internal sales teams and external prospects. To be successful in this role you will be an exceptional people leader with proven experience managing managers across multiple workstreams, and a natural ability to influence at the executive level. The ideal candidate will bring a strong analytical mindset, deep familiarity with enterprise B2B sales cycles, and a passion for building scalable, repeatable processes that deliver measurable business outcomes.

Requirements

8–10 years of experience in Technical Solution Selling, Customer Success, Sales Engineering, or Professional Services.
5+ years of direct people management experience, including a proven track record of managing other people leaders and multiple work groups.
Demonstrated experience leveraging AI or automation technologies to drive operational efficiencies within a Revenue Support or Sales Operations environment.
Deep understanding of complex enterprise B2B sales cycles and methodologies such as MEDDPICC or CHAMP.
Strong analytical acumen with the ability to use data to communicate business impact to executive stakeholders.
Exceptional leadership, negotiation, and relationship management skills with experience navigating cross-functional and executive partnerships.
Willingness to travel occasionally for business purposes.

Responsibilities

Oversee a high-performing team composed of both people leaders and specialized individual contributors, ensuring alignment with established business policies and result targets.
Manage departmental activities through a tiered leadership structure, balancing high-level mentorship of managers with tactical oversight of critical individual workstreams to ensure operational excellence.
Manage the coordination of activities across the Pilot Success and Route Optimization teams, taking responsibility for results, costs, and methods.
Lead strategic planning and change management initiatives to ensure the team meets evolving business objectives and revenue targets.
Align technical resources across specialized pilot workstreams to ensure high-priority enterprise accounts receive expert support.
Develop and execute an AI implementation roadmap to automate manual workflows in pilot data analysis, reporting, and hardware provisioning.
Drive continuous process improvements to ensure standardized, repeatable, and scalable operations.
Leverage AI to enhance telematics data interpretation, providing faster and more accurate ROI demonstrations to prospective customers.
Shift team effort from manual data processing to high-value strategic consulting through the use of automated predictive insights.
Own the "Customer Journey" for the pilot phase, partnering with Product and UX teams to reduce technical friction and enhance the user experience.
Champion a robust feedback loop from the field to the Product organization, synthesizing pilot insights to de-risk research and development efforts.
Translate pilot successes and process innovations into valuable sales assets, such as case studies and best practice guides, in partnership with Marketing.
Standardize the Pilot Experience to ensure consistent brand and service delivery across different markets and industry segments.
Act as the senior point of escalation for high-stakes pilot engagements and critical customer issues.
Define and analyze high-level program KPIs, including pilot influence on win rates, reduction in sales cycle time, and direct contribution to revenue goals.
Help build reporting structures that prove the Pilot Program's direct correlation to Annual Recurring Revenue (ARR) and Customer Lifetime Value (CLV).
Enable Sales and Solutions Engineering leadership on strategic pilot positioning and success planning for large enterprise accounts.