Senior Manager, Pilot Success
Who we are:
Who you are:
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!
What you'll do:
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.
How you'll make an impact:
- 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.
What you'll bring to the role:
- 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.
Why job seekers choose Geotab:
Flex working arrangements
Home office reimbursement program
Baby bonus & parental leave top up program
Online learning and networking opportunities
Electric vehicle purchase incentive program
Competitive medical and dental benefits
Retirement savings program
*The above are offered to full-time permanent employees only
How we work:
Other employment statements:
Geotab will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. Additionally, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the Company's legal duty to furnish information.
We are committed to accommodating people with disabilities during the recruitment and assessment processes and when people are hired. We will ensure the accessibility needs of employees with disabilities are taken into account as part of performance management, career development, training and redeployment processes. If you require accommodation at any stage of the application process or want more information about our diversity and inclusion as well as accommodation policies and practices, please contact us at careers@geotab.com. Geotab provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability or genetics. In addition to federal law requirements, Geotab complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training. Geotab expressly prohibits any form of workplace harassment or discrimination based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of Geotab's employees to perform their job duties may result in discipline up to and including discharge. If you would like more information about our EEO program or wish to file a complaint, please contact our EEO officer, Klaus Boeckers at HRCompliance@geotab.com. For more details, view a copy of the EEOC's Know Your Rights poster. By submitting a job application to Geotab Inc. or its affiliates and subsidiaries (collectively, “Geotab”), you acknowledge Geotab’s collection, use and disclosure of your personal data in accordance with our Privacy Policy. Click here to read our Privacy Notice.Apply for this job
*
indicates a required field