Customer Success Manager

Wholesail·Remote(United States)
Customer Success

WFA Digital Insight

The demand for skilled customer success managers in fintech has grown significantly, with over 25% of companies planning to expand their customer success teams in the next year. Wholesail is at the forefront of this trend, building a financial network for wholesale trade that automates payments, credit, and reconciliation workflows. With a strong focus on digital skills and remote work, this role is ideal for those who want to drive real business outcomes and work with sophisticated customers. As the remote job market continues to evolve, candidates with experience in SaaS and a strong understanding of accounting systems are in high demand. Before applying, candidates should be aware of the complex technical environment and the need for strong business acumen.

Job Description

About the Role

The Customer Success Manager role at Wholesail is a unique opportunity to work with a fast-moving team that is solving hard problems at the intersection of fintech, accounting, and enterprise software. As a Customer Success Manager, you will be responsible for driving financial results for your customers and for Wholesail, partnering closely with the Sales, Product, and Onboarding teams to advise on customer priorities and drive long-term value. You will operate in an intellectually rigorous environment where new ideas and contributions are encouraged, and you will have the ownership and challenge to do your best work.

The role requires a deep understanding of complex accounting systems and operational workflows, as well as the ability to leverage AI and cutting-edge technologies to drive business outcomes. You will be working with a sophisticated customer base, including Controllers, CFOs, and CEOs, and you will need to be able to communicate complex technical subjects in a clear and structured way.

Wholesail is committed to building a customer-centric team, and as a Customer Success Manager, you will be a key part of this effort. You will be responsible for driving customer satisfaction and retention, and you will work closely with the product team to provide feedback and help shape the future of the company's customer success function.

What You Will Do

  • Operate as the CEO of your own book of accounts to drive financial results for your customers and for Wholesail
  • Partner closely with the Sales, Product, and Onboarding teams to advise on customer priorities and drive long-term value
  • Leverage AI and cutting-edge technologies to drive business outcomes and improve customer satisfaction
  • Handle a complex book of accounts that integrate with various ERPs, including QuickBooks, NetSuite, and Entree
  • Lead executive-level conversations with Controllers, CFOs, and operators to drive business outcomes and improve customer satisfaction
  • Uncover root operational and accounting challenges through deep discovery and provide solutions to drive business outcomes
  • Handle escalations independently with a clear point of view and identify churn risk early to create structured mitigation plans
  • Work closely with the product team to provide feedback and help shape the future of the company's customer success function
  • Develop and execute a strategic plan to drive customer satisfaction and retention
  • Collaborate with the sales team to identify new sales opportunities and drive revenue growth

What We Are Looking For

  • 3-5+ years of experience in SaaS, preferably in a technically complex environment
  • Background as a Customer Success Manager, Account Manager, or Solutions Engineer, handling high-value customers
  • Strong business acumen and comfortable communicating with Controllers, CFOs, CEOs, and operators
  • Clear, structured communication skills, both written and verbal
  • Comfort discussing technical subjects internally and externally
  • History of increasing responsibility or fast growth in a previous role
  • Experience with ERPs, product integrations, and accounting concepts
  • Strong analytical and problem-solving skills, with the ability to think critically and creatively
  • Ability to work in a fast-paced environment and prioritize multiple tasks and projects

Nice to Have

  • Experience with AI and machine learning technologies
  • Knowledge of accounting principles and financial systems
  • Certification in a related field, such as CPA or CMA
  • Experience working in a remote or distributed team environment
  • Familiarity with Agile development methodologies and project management tools

Benefits and Perks

  • Competitive compensation and meaningful equity
  • Opportunity to work with experienced tech startup founders and a customer-centric team
  • Medical, dental, and vision insurance, as well as short-term and long-term disability insurance
  • 401(k) or other retirement plan with company match
  • Flexible PTO and vacation policy
  • Remote work stipend and home office setup support
  • Professional development and continuing education opportunities
  • Access to the latest tools and technologies, including AI and machine learning platforms
  • Recognition and reward programs for outstanding performance and contributions

How to Stand Out

  • Tip: Make sure you have a strong understanding of accounting principles and financial systems, as well as experience with ERPs and product integrations.
  • Be prepared to discuss your experience with AI and machine learning technologies, and how you can leverage them to drive business outcomes.
  • Highlight your ability to communicate complex technical subjects in a clear and structured way, both written and verbal.
  • Emphasize your experience working with sophisticated customers, including Controllers, CFOs, and CEOs.
  • Show your ability to think critically and creatively, and to prioritize multiple tasks and projects in a fast-paced environment.
  • Research the company and the role, and be prepared to ask informed questions during the interview process.
  • Be prepared to provide specific examples of your experience and accomplishments, and to explain how you can contribute to the company's success.

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