Senior Manager, Pilot Success

Geotab•Oakville, ON

16d•Hybrid

About The Position

Geotab ® is a global leader in IoT and connected transportation and certified “Great Place to Work™.” We are a company of diverse and talented individuals who work together to help businesses grow and succeed, and increase the safety and sustainability of our communities. Geotab is advancing security, connecting commercial vehicles to the internet and providing web-based analytics to help customers better manage their fleets. Geotab’s open platform and Geotab Marketplace ®, offering hundreds of third-party solution options, allows both small and large businesses to automate operations by integrating vehicle data with their other data assets. Processing billions of data points a day, Geotab leverages data analytics and machine learning to improve productivity, optimize fleets through the reduction of fuel consumption, enhance driver safety and achieve strong compliance to regulatory changes. Our team is growing and we’re looking for people who follow their passion, think differently and want to make an impact. Ours is a fast paced, ever changing environment. Geotabbers accept that challenge and are willing to take on new tasks and activities - ones that may not always be described in the initial job description. Join us for a fulfilling career with opportunities to innovate, great benefits, and our fun and inclusive work culture. Reach your full potential with Geotab. To see what it’s like to be a Geotabber, check out our blog and follow us @InsideGeotab on Instagram. Join our talent network to learn more about job opportunities and company news. We are always looking for amazing talent who can contribute to our growth and deliver results! 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.