Full-Time

Director of Customer Success

Updated on 8/19/2026

Cardata

Cardata

51-200 employees

Mileage tracking and vehicle reimbursement software

Compensation Overview

CA$115k - CA$135k/yr

+ $20,000-$40,000 performance-based additional earnings

Remote in Canada

Remote

Category
Customer Experience & Support (1)
Required Skills
CRM
HubSpot
Salesforce
Gainsight
Data Analysis

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Requirements
  • At least 8 years of experience in Customer Success or a Customer Experience-related Software as a Service function.
  • At least 4 years of people leadership experience, including coaching and holding experienced customer-facing professionals accountable.
  • Demonstrated success improving customer retention, adoption, health, and team performance.
  • Experience leading teams through organizational growth, operational change, or evolving processes.
  • Ability to prioritize, simplify work, and improve outcomes in a resource-conscious environment.
  • Experience establishing Customer Success operating cadences, performance measures, and scalable processes.
  • Strong strategic account management and executive customer engagement experience.
  • Experience leading or closely partnering with Implementation and Customer Success Operations.
  • Ability to turn reporting and customer data into meaningful insights and action.
  • Strong cross-functional leadership skills, particularly with Sales, Account Management, Product, Engineering, Support, and Finance.
  • Practical experience using artificial intelligence and automation to improve personal productivity, team effectiveness, or customer workflows.
  • Strong executive communication, analytical thinking, judgment, and follow-through.
  • Experience with Gainsight, Salesforce, HubSpot, or a comparable Customer Success or customer relationship management platform.
Responsibilities
  • Lead, coach, and develop the Customer Success, Implementation, and Customer Success Operations teams.
  • Establish clear performance expectations, operating cadences, and accountability across the organization to drive customer adoption, value realization, executive engagement, retention, and renewal readiness.
  • Ensure customer risks are identified early and supported by actionable recovery plans.
  • Provide executive sponsorship for strategic, complex, and at-risk customer relationships.
  • Oversee the new-customer implementation experience, including launch quality, time-to-value, training, and handoff into Customer Success.
  • Partner with Customer Success Operations to improve Customer Success Manager enablement, reporting, portfolio insights, data quality, workflows, and the Customer Success knowledge base.
  • Use customer and operational data to identify trends, prioritize action, and provide clear recommendations to executive leadership.
  • Identify opportunities to simplify processes, automate manual work, and return capacity to strategic customer engagement.
  • Establish practical expectations for how artificial intelligence should be used across Customer Success to improve preparation, analysis, communication, and workflow efficiency.
  • Partner closely with Account Management, Support, Sales, Product, Engineering, Finance, and Operations.
  • Represent the customer perspective in company planning and product-prioritization discussions.
  • Build a high-performance culture grounded in ownership, sound judgment, transparency, and continuous improvement.
Desired Qualifications
  • Gainsight experience is a plus.

Cardata provides a software platform and consulting services to manage vehicle reimbursement and risk for employees using personal cars for work. Its core product automates mileage tracking and reimbursements via a mobile app, with management reporting and analytics, and it integrates with expense systems like SAP Concur. The service emphasizes compliance with tax and insurance rules to ensure fair, accurate reimbursements and reduce risk, while offering customized consulting to design vehicle-reimbursement programs. Its goal is to simplify administration, cut tax waste, and help organizations of all sizes manage a mobile workforce efficiently.

Company Size

51-200

Company Stage

Growth Equity (Venture Capital)

Total Funding

$73.3M

Headquarters

Boston, Massachusetts

Founded

1999

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Simplify Jobs

Simplify's Take

What believers are saying

  • Wavecrest and MassMutual backed Cardata with $100 million in September 2023.
  • Cardata Intelligence launched in July 2025 and expanded reporting for every customer in 2026.
  • Winnie Chen joined as Vice President of Growth on January 2, 2026, signaling sales expansion.

What critics are saying

  • Concur and expense-suite vendors can bundle mileage workflows and compress Cardata's pricing by 2026.
  • Cardata's AI reporting claims invite copycats; faster rivals can neutralize the 2025 launch quickly.
  • A compliance failure or IRS challenge on reimbursement methodology would damage trust and trigger churn.

What makes Cardata unique

  • Cardata combines mileage reimbursement software, compliance programs, and managed services across U.S. and Canada.
  • Its 2025 Cardata Intelligence launch adds AI reporting, alerts, and natural-language analytics for finance teams.
  • SAP Concur integration and dedicated compliance support make switching costs higher than standalone mileage apps.

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Benefits

Health Insurance

Dental Insurance

Remote Work Options

Flexible Work Hours

Health Savings Account/Flexible Spending Account

Wellness Program

Paid Vacation

Paid Sick Leave

Paid Holidays

Professional Development Budget

Growth & Insights and Company News

Headcount

6 month growth

5%

1 year growth

2%

2 year growth

0%
PR Newswire
Sep 28th, 2023
Cardata Raises $100M In Capital To Accelerate Growth And Investment In Product Innovation

TORONTO, Sept. 28, 2023 /PRNewswire/ -- Cardata , a leading provider of tax-compliant mileage reimbursement software to leading global organizations, today announced a new round of growth investment led by Wavecrest Growth Partners, with participation from MassMutual Ventures.Founded in 1999, Cardata provides a suite of reimbursement software, compliance programs, and business intelligence tools for companies whose employees drive their personal cars for work.Over the past three years, under the leadership of Sheret Ross and Michael Levine, Cardata has tripled its annual recurring revenue, growing by over 200% in aggregate. Cardata is on track for another record breaking revenue growth year. This latest strategic investment will accelerate the Company's market coverage and pace of innovation in both its core systems and new products, enabling it to continue to support its rapidly growing customer base.Sheret Ross, CEO at Cardata, said, "Companies are turning to more efficient vehicle programs to deliver benefits and savings to their employees. As Cardata has helped tens of thousands of drivers get reimbursed for using their personal car for work, we aim to unlock more value for our users and expand our market coverage. This strategic investment from Wavecrest and MassMutual will accelerate the pace of our product innovation and help us continue to deliver a superior experience, along with new products, for our users."Michael Levine, President at Cardata, said, "This significant investment represents a pivotal moment in our company's journey

FinSMEs
Mar 26th, 2021
CarData Consultants Secures Growth Investment From Spruce Grove Capital

CarData Consultants, an Oakville, Ontario, Canada-based provider of vehicle reimbursement software, secured a growth investment from Spruce Grove Capital. The amount of the deal was not disclosed. The company intends to use the funds to accelerate its continued expansion within the corporate vehicle reimbursement market throughout North America. Founded in 1999 by John Domsy, CarData provides […]