Full-Time

Customer Success Manager

Cardata

Cardata

51-200 employees

Mileage tracking and vehicle reimbursement software

Compensation Overview

CA$70k - CA$80k/yr

Remote in Canada

Remote

Remote within Canada, with occasional travel two to three times per year.

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

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Requirements
  • Three to five years of experience in a customer-facing role such as Customer Success, Account Management, or Consulting, ideally in Software as a Service.
  • Proven success managing mid-to-large enterprise accounts with multiple stakeholders.
  • A demonstrated track record of driving retention, adoption, and expansion across a diverse portfolio.
  • Experience leading executive-level conversations and influencing decision-making.
  • Experience leading customer conversations, including business reviews, strategic planning sessions, renewals, and expansions.
  • Skill in data-driven storytelling using metrics to demonstrate value and influence outcomes.
  • Strong negotiation skills.
  • Technical proficiency and experience working in remote-first environments.
  • Confidence leading C-level conversations and influencing high-stakes decisions.
  • The ability to synthesize insights and create actionable insights to drive customer outcomes.
  • The ability to manage complex programs, negotiations, and stakeholder expectations.
Responsibilities
  • Own a portfolio of strategic accounts and deliver measurable outcomes that drive customer return on investment.
  • Lead consultative onboarding and successful program implementations, ensuring executive alignment and using established playbooks and processes.
  • Drive revenue growth across the portfolio through increased adoption, program optimization, and successful renewals.
  • Monitor engagement, program performance, and usage trends to ensure customers realize value from their program.
  • Identify and drive opportunities to expand Cardata’s programs within existing accounts based on customer goals, usage insights, and organizational changes.
  • Build trusted relationships with executives, program administrators, Human Resources leaders, and finance partners.
  • Lead executive business reviews and quarterly business reviews that showcase data-backed value and growth opportunities.
  • Collaborate cross-functionally to deliver seamless customer experiences while championing customer needs in alignment with Cardata’s growth objectives.
  • Create and deliver engagement strategies that deepen adoption, sustain long-term value, and strengthen customer loyalty.
  • Drive end-to-end renewal cycles, negotiate terms, and secure multi-year commitments where possible.
  • Work proactively with customers to address challenges and ensure programs continue delivering value ahead of renewal cycles.
  • Partner with leadership to refine customer segmentation, playbooks, and success frameworks that scale across the organization.
  • Collaborate cross-functionally with Product, Sales, Operations, and Support to streamline processes and improve the customer experience.
  • Drive renewals for accounts within the portfolio and lead renewal conversations with customer stakeholders.
  • Monitor customer health indicators and identify early signs of risk or disengagement.

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 […]