Senior Director of Customer Success

Job description

About Us

AdvicePay is a billing and payment processing platform that enables financial advisors to shift their focus toward giving advice to people still building wealth, instead of only those who already have it. Historically, financial planning advice was only available to the affluent, who could afford to pay a financial advisor’s fees directly from their portfolios. We set out to change that, as we believe personal financial planning advice should be available to all. In doing so, we’ve become the very first and only technology solution created specifically for fee-for-service financial planning.

We are headquartered in Bozeman, Montana (and recently re-opened our office with safety protocols in place, though most of our team continues to work from home due to COVID-19). Our sister company, XY Planning Network, was nationally recognized as one of The 346 Best Places to Work in 2019 by Inc. magazine and by the 2019 InvestmentNews Excellence in Diversity & Inclusion Awards. And since we work in the same office and have the same awesome benefits and core values, we like to say “we basically won too!”

You’ll love working here if you value - and want to contribute to - a positive, inclusive, innovative, and “Get Sh*t Done” culture where teammates help one another succeed and are committed to doing the right thing. If you're up for the challenge of disrupting an industry, join us!

About the Platform

Users of AdvicePay are financial advisors who use our platform to get paid by their clients for fee-for-service financial planning. Advisors can issue agreements for client e-signature, accept ACH and credit cards, bill hourly or one-time fees, and establish recurring subscription payments while remaining fully compliant with current industry regulations.

About the Position

The Senior Director of Customer Success role is a newly created leadership position responsible for all aspects of our current customer relationships. Working with our CEO, Managing Director, and leadership across the company to help our users adopt and rave about AdvicePay, this position will own and execute on the vision, strategy, and day-to-day tactics that we employ to take our scaling organization (that is more than a little obsessed with its users!) to the next level.

Our Customer Success department is fundamental to the overall achievement of our company, because we are nothing without our customers. Currently composed of two primary pillars -- Technical Support and Relationship Management -- team members in this department have a wide range of unique accountabilities. We’re excited about you because you’re intimately familiar with the traditional duties of both support and account management, knowing how to effectively integrate and work between the two so that together they are a powerhouse for customer satisfaction, retention, adoption, and growth. 

(Among the things you’ll do best? Empowering our users to succeed -- and expand -- on our platform by coaching team members on how to effectively communicate our value proposition and successfully guide customers in adopting our best practices.)

We don’t believe happy, successful customers are born out of thin air or by luck! It comes from hard -- and smart -- work, radical empathy, and having the Right People in the Right Seats. You’ll find you’re a perfect fit for this role if you like “thinking big” and have successfully led customer success programs, including: hiring and developing relationship management + technical support professionals, building and refining customer success strategies and best practices, driving customer delight, engagement, and expansion through the execution of strategic objectives, and setting smart metrics while holding the team accountable for both effort and results. 

If by now you’re saying, “This sounds like me!” ...well, we can’t wait to meet you!

What You’ll Do

  • People Management
    • Oversee all team members on the Customer Success team (currently 5 people with plans to expand)

    • Conduct weekly 1:1 meetings with every direct report you manage

    • Conduct weekly Customer Success team meetings, using the EOS format from the book Traction (Don’t worry, we will train you on this!)

    • Attend weekly department head meetings, representing our Customer Success Team, bringing up issues and helping determine solutions to propel us forward

    • Manage the recruiting, hiring, onboarding, and mentoring process for new hires on your team

    • Give and receive thoughtful feedback in an effort to produce high-quality work

    • Champion an inclusive, healthy team environment that fosters trust and a sense of empowerment

  • Define and grow our Customer Success program
    • Implement initiatives that support the entire post-conversion customer lifecycle, including big areas like Enterprise onboarding

    • Develop and deploy strategies aimed at influencing monthly recurring revenue + customer lifetime value (via higher feature adoption, customer satisfaction, and increasing user counts)

    • Track trends in client satisfaction (NPS) metrics, making sound judgements about changes needed to maintain high-levels of happiness, encourage product adoption, and mitigate churn

    • Ensure we are providing top-notch tech support and self-help documentation, oversee staffing to meet Enterprise-level SLAs, and take the lead to swiftly resolve escalating customer issues

    • ​​Stay up-to-date on customer experience best practices in the SaaS field, driving thought leadership involving the future of Customer Success at AdvicePay

  • Become an AdvicePay wizard -- so you can use your magic to be helpful to both customers and team members!

  • Dive in with the people you lead, actively helping to reinforce bandwidth on a project level in areas like new feature rollouts, content creation, etc (getting your hands dirty to knock out great work comes naturally to you -- you may even have a hard hat to prove it)

  • Manage Enterprise-level renewal cycles and one-off feature build agreements, dotting the i’s and crossing t’s to ensure contracts/SOWs are accurate, complete, and signed

  • Collaborate across departments to identify + fix gaps in customer-facing or internal processes, helping ensure a swoon-worthy customer experience at every click, email, phone call, training demo, webinar, and conference

  • Provide your keen customer insight to Product teams, unveiling opportunities to improve our user experience and/or product features

  • Partner with our Sales team to transition signed Enterprise contracts to Customer Success, execute successful onboarding/implementation, and align on strategies for new customer growth

  • Manage the annual conference schedule/strategy for relevant Customer Success team members (of course, when conferences and travel are back to normal)

  • Maintain internal metrics and produce weekly, monthly, and quarterly performance reports, analyzing and presenting them for department-level and company-level meetings

Key Metrics for Success

  • NPS Score

  • Transaction Volume

  • Enterprise Advisor User Growth

  • Feature Adoption

The Deets

  • Start Date: Immediately
  • Status: Full-time (40-45 hours per week)
  • Location: Bozeman, MT 
  • Department: Customer Success
  • Reports to: Lucy Robeson, Managing Director
  • Direct Reports: Yes; 4 team members

Compensation & Benefits

  • Salary: $101,334/year, based on accountabilities for this position and our transparent salary structure shared with all team members during their first week

  • Unlimited vacation days to maintain work-life harmony (we require you to take a minimum of 3 weeks of vacation per year)

  • 10 paid holidays when the office is closed

  • 401(k) with match - you put in 6% and we put in 4.5%

  • 12 weeks of paid maternity/paternity leave for the birth or adoption of a child

  • Health benefits package provided of up to $500/month

  • Dental, Vision, Voluntary Life and AD&D, and Accident insurance options

  • Employer-paid life insurance

  • Employer-paid long-term disability coverage

  • $600/year to cover the cost of working with a financial planner, plus up to $500 toward the one-time upfront fee

  • $250/quarter to spend on yourself specific to our core value of “Be Well Being You”

  • $500 donated to a non-profit organization of your choice when you volunteer 40 hours/year

  • $2,000/year in Professional Development funds

  • A sabbatical program that includes a cash bonus and extra time off at 5, 10, and 15 years

  • Subsidized employer-sponsored childcare through our internal daycare program

  • Company-owned MacBook Pro provided

  • $5,000 relocation package available to those moving to Bozeman, MT

  • Please see our Dream Team Handbook for more info about the benefits and perks we offer!


What You’ll Bring to the Table (If you think, “I only meet 80% of these qualifications," still apply!)

  • 5+ years experience in a Customer Success/Experience related role, with 3+ years experience leading and scaling success teams

  • A proven playbook for implementing best practices that drive feature adoption and enhance the customer experience

  • An unrivaled customer-first mentality. You are a tireless cheerleader for doing the right thing for the customer, with the conviction that a successful customer is one making the best use of the product they’re paying for!

  • A bottomless well of patience and empathy for customers (but not a doormat)

  • Familiarity with subscription and renewal-based business processes, upselling, cross-selling, and/or expansion sales strategies within the customer success framework

  • Ability to set clear, measurable goals for your team, as well as determine how you measure your team’s success

  • A data-driven love for figuring out how proactive, scalable customer support can impact user growth, feature adoption, and churn -- and then acting on it

  • Energy and excitement when working in a new, fast-paced environment with a lot of unknowns (no Tums needed)

  • Superlative communication skills, with the ability to convey information with warmth and clarity over email, Slack, Zoom, etc.

  • A love of detailed work that requires both accuracy and consistency -- nothing falls through the cracks on your watch!

  • Strong tech-savvy and the ability to effortlessly pick up new technology

  • Comfort in speaking to both small and large audiences (perhaps without having to imagine dozens of pairs of underwear...)

  • An understanding of and strong alignment with our core values

  • Proven ability to work closely and harmoniously, while maintaining cohesion, across multiple team members and several departments

  • Cooperative, dependable work ethic and a high sense of personal responsibility and integrity

  • Legally authorized to live and work in the United States

What Will Make Us Drool

  • Financial planning or financial services knowledge

  • Experience working within SaaS, Fintech, or Payments

  • Experience on a team using the Entrepreneurial Operating System (EOS)


  • Cover Letter (text to be copied into the application form)
  • Resume (to be uploaded)
  • Applications will be reviewed as they are received


  • Initial screen answering a few short questions about AdvicePay and the position. After applying, please be on the lookout for an email from us on next steps! (It may get caught up in your Junk folder or a Promotions tab.)

  • First-round interview

  • Work sample

  • Final round interviews, including:
    • Meet some of the team members
    • Company’s core values interview
    • Final interview with Managing Director and/or CEO
  • Our typical hiring process takes 6-8 weeks from when we first post the job to when we extend a final offer

AdvicePay believes that our team members, and the individual identities and experiences of our team members, are our key differentiators. We won't settle for mere acceptance of each other's differences because we maintain that our team is better because of our differences, not in spite of them. As such, our culture celebrates, champions, supports, protects, and thrives on our various and collective identity categories. AP is beyond proud to be an equal opportunity employer.