VP of Customer Success

Sorry, this job was removed at 08:09 p.m. (CST) on Wednesday, Sep 10, 2025
Hiring Remotely in USA
Remote
Insurance • Software
Sure's enterprise SaaS platform and APIs simplify the sales and service of digital insurance.
The Role
Join Sure: Building the Rails of Digital Insurance
Founded in 2015, Sure is the insurance technology leader unlocking the potential of digital insurance. We're building the digital infrastructure that powers insurance transactions between carriers, brands, and consumers. Today, only 1% of insurance transactions are truly digital, representing a $6 trillion market opportunity. Are you up for the challenge?

How We Do It
We work with insurance carriers to enable their offline-to-online transitions as well as non-insurance companies who want to launch embedded digital insurance programs. As a Software as a Service (SaaS) provider, we serve as the essential technology backbone for the digital insurance ecosystem.

Why join our team?
🌐 Remote-first culture. We work from home and embrace digital collaboration
💥 Impactful work: We're transforming a trillion-dollar industry that touches everyone's lives
🏆 Award-winning growth: Named among Deloitte Technology Fast 500, Inc. 5000, Forbes Fintech 50, and CNBC World's Top Insurtech Companies
🤝 Culture is everything. Join an incredible team of smart, passionate, collaborative and driven individuals.

We’re growing!
We're seeking our first Customer Success hire - a hands-on Customer Success leader who will own the retention, optimization, and monetization of our enterprise customer base. As our founding Customer Success team member, you'll establish Sure as an indispensable partner through your direct customer relationships while simultaneously building the foundation and vision for the Customer Success department you'll eventually lead. This role is perfect for someone who understands the value of the start up “builder” mentality, thrives in a consultative, high-touch enterprise environment, can serve as a trusted advisor to C-suite executives, and has the strategic vision to build and scale a world-class Customer Success organization from the ground up. 

What you'll be doing:

  • Including, but not limited to:
  • Revenue Growth, Retention and Expansion
  • Own net dollar retention (NDR) and GWP generation targets across our existing customer base
  • Drive revenue growth through hands-on program optimization and account management
  • Directly identify and execute expansion opportunities within your account portfolio
  • Lead upsell initiatives by introducing complementary products and programs

  • Hands-On Program Success & Adoption
  • Personally guide newly launched programs to ensure rapid adoption, success, and growth
  • Work directly with partners and programs to reach the "tipping point" where material revenue and regulatory complexity ensure long-term retention
  • Serve as the hands-on strategic advisor and primary contact point helping customers optimize their insurance program performance

  • Customer Engagement
  • Personally maintain relationships with C-suite executives at major enterprise accounts
  • Balance customer advocacy with Sure's business objectives in every interaction
  • Establish yourself as the trusted expert resource and extension of each customer's team

  • Foundation Building & Process Creation
  • Create scalable playbooks for account growth and expansion based on your direct experience
  • Document processes, best practices, and learnings that will become team standards
  • Establish the foundational workflows and systems that will scale as we grow
  • Partner with executive leadership to define CS KPIs and reporting based on real results

What we're looking for:

  • 10+ years of hands-on customer success, account management, or related roles with experience personally managing enterprise accounts with complex, multi-stakeholder relationships
  • 3+ years of experience building and leading customer success teams from early stages years
  • Proven track record as an individual contributor and team builder driving revenue growth and retention
  • Demonstrated success scaling Customer Success organizations from 1-10+ team members
  • Comfortable making tough decisions and having difficult conversations directly with customers
  • Experience with consultative selling and solution-based approaches
  • Deep understanding of SaaS metrics (NDR, GRR, NPS, etc.) from hands-on experience
  • A self-starter who can see the future organization while executing today's priorities

What we do for you:

  • Unlimited PTO… no really, we want you to take it!
  • Mental Health Breaks - company provided meditation app and a weekly wellness hour
  • WFH stipend to help you work your best while being remote
  • Countless Medical, Dental and Vision plans … we are an insurtech company after all!
  • Equity and 401K
  • Generous parental leave

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

For more information, visit https://www.sureapp.com/. Follow @SureHQ on Twitter, Facebook and Instagram.    

Employment at Sure is contingent upon a satisfactory verification of a general and criminal background check and education and employment verification. Upon an offer of employment, all prospective employees may be required to complete an employment application. Any background verifications will be obtained with written consent from the individual.

Sure Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sure and has not been reviewed or approved by Sure.

  • Healthcare Strength Healthcare coverage is described as comprehensive, with medical, dental, and vision options for employees and dependents and a broad menu of plan choices. Employer premium contributions and numerous plan options are presented as a differentiator versus leaner startup benefits.
  • Leave & Time Off Breadth Time off is positioned as generous through an unlimited PTO policy that is framed as intended to be used. The package also includes flexibility elements associated with remote-work support.
  • Equity Value & Accessibility Equity is described as being offered broadly to employees, increasing perceived access to ownership upside. This can strengthen total rewards even when cash compensation is described as mid-market rather than top-of-market.

Sure Insights

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The Company
180 Employees
Year Founded: 2014

What We Do

Sure is an insurance technology company that powers digital programs for the world’s most recognized brands and carriers. Its enterprise SaaS Platform and APIs accelerate digital transformation and omnichannel distribution. Sure streamlines all aspects of digital insurance sales and service for each phase of the insurance life cycle.

Why Work With Us

Each and every one of us cares deeply about the success of Sure and have a tremendous amount of pride in our work. We are unconstrained by how things may have been done in the past and are committed to innovation and growth, both individually and as a team. Most importantly, we like each other!

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