Flex is building the AI-native private bank for business owners. We’re re-architecting the entire financial system for entrepreneurs—from the first dollar a business earns to how that value compounds, moves,...

Flex is building the AI-native private bank for business owners. We’re re-architecting the entire financial system for entrepreneurs—from the first dollar a business earns to how that value compounds, moves,...

We believe that mental health is just as important as physical health. We recognize that mental health issues can be complex and multifaceted, and we are dedicated to treating the whole person, not just the symptoms.

We aim to create a world where mental health is no longer stigmatized or marginalized, but rather is embraced as an integral part of one’s overall well-being.

We believe that by providing quality care that is both evidence-based and compassionate, we can empower individuals to take charge of their mental health and achieve their full potential. We are passionate about making a positive impact on the lives of those struggling with mental health issues and we strive to be a force for positive change in the field of mental healthcare.

Rula is a remote-first company. We currently hire in most U.S. states, with the exception of Hawaii.

About the Role

We are seeking a Director of Finance Systems to own the technology behind Rula’s accounting and financial reporting, and to help our Accounting team move toward a faster, more automated close. This is a chance to shape how a fast-growing mental health company runs its finances, with a scope that goes well beyond ERP administration and into AI, automation, and the controls that let us scale with confidence.

You will oversee our core finance systems, including NetSuite, Ramp, Zip, FloQast, and revenue reporting tools. You will be the project manager for new system launches and updates, and you will partner with Engineering to make sure Finance’s needs are built in from the start. You will also set our approach to AI: how our Accounting team builds agents, where they run, how they connect to NetSuite, and what safeguards keep them accurate and audit-ready. You will lead the build-out of ITGC and financial systems controls that keep pace with the business as it scales.

This role sits at the intersection of finance, systems, and AI, and works closely with Accounting, FP&A, Financial Operations, Procurement, Product, Engineering, and Analytics. You will report directly to the Controller and join a collaborative team that is already experimenting with AI and wants a partner to help turn those ideas into dependable tools.

Required Qualifications

• 10+ years of experience in finance systems, accounting systems, or ERP administration, including hands-on ownership of NetSuite in a growing company.

• Has led at least one finance system implementation or post-go-live stabilization from requirements through testing, cutover, and support.

• Hands-on experience designing, implementing, or maintaining IT general controls (user access, change management, system operations) for systems used in financial reporting, in an audit-ready environment.

• Has owned or governed a chart of accounts and has built reports or saved searches in NetSuite (or a comparable ERP) for accounting users.

• Track record of partnering with Accounting, Procurement, and Engineering or Product teams to turn business needs into system workflows and integrations.

• Can explain technical systems, risks, and tradeoffs clearly to non-technical colleagues, in writing and in conversation.

Preferred Qualifications

• Has built or deployed AI agents or automated workflows in a finance or accounting setting, including permissions, human review, and audit logging.

• Experience implementing or administering a procurement or spend platform (Zip, Coupa, Ramp).

• Experience with healthcare billing or revenue cycle systems (claims, remittances, contractual adjustments).

• Working knowledge of SQL or SuiteQL, and of planning or reporting tools such as Pigment or Hex.

• Relevant credentials such as NetSuite Administrator or ERP Consultant certification, CPA, or CISA.

• Background in a high-growth startup or digital health company.

We’re serious about your well-being! As part of our team, full-time employees receive:

• 100% remote work environment: Working hours to support a healthy work-life balance, ensuring you can meet both professional and personal commitments (must be based in United States, currently not hiring in Hawaii)

• Attractive pay and benefits: Full transparency of pay ranges regardless of where you live in the United States

• Comprehensive health benefits: Medical, dental, vision, life, disability, and FSA/HSA

• 401(k) plan access: Start saving for your future

• Generous time-off policies: Including 2 company-wide shutdown weeks each year for self-care (for most employees)

• Paid parental leave: Available for all parents, including birthing, non-birthing, adopting, and fostering

• Employee Assistance Program (EAP): Supporting your mental and physical health

• Quarterly department stipend: Fun team-building activities or in-person gatherings

• Community and employee resource groups: Participate in groups that celebrate employee identity and lived experiences, fostering a sense of community and belonging for all

• Home office stipend: New hire home office stipend & $50 monthly stipend to help cover internet or cell phone expenses

• Wellness at Rula program: Year-round wellness initiatives and a $50/month wellness stipend

Our team

We believe that diversity, equity, and inclusion are fundamental to our mission of making mental healthcare work for everyone.  We are dedicated to having a culture of inclusion that will support our employees in feeling safe, seen, heard, and valued.

Headquarters: Nevada, Remote

Chief Risk Officer (CRO) – Sezzle Bank

Location: Nevada / Remote

Organization: Sezzle Bank (in formation)

Employment Type: Full-time | Remote

Reports To: President of Sezzle Bank and the Board Risk and Compliance Committee

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless installment plans that make shopping smarter and more accessible. We're not just transforming payments; we're redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we're building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you're excited about breaking new ground in tech and building products that make a real difference for consumers and merchants alike, come join us at Sezzle.

About Sezzle Bank (in formation):

Sezzle Bank is a planned de novo national bank in formation, headquartered in Nevada and wholly owned by Sezzle Inc. The Bank will serve as the regulated banking entity supporting Sezzle's financial product offerings and ancillary services, with a strategic focus on responsible lending, financial innovation, and exceptional customer experience. We are building a best-in-class team to stand up a safe, sound, and compliant institution from the ground up.

About the Role:

We are seeking a highly experienced Chief Risk Officer to develop and maintain an effective, independent second-line risk management program for Sezzle Bank. The CRO will measure and manage credit, market, liquidity, and operational risk — with operational risk encompassing legal, compliance, and technology risk — as well as model-related risk across the Bank. Working with the Board and the Board Risk and Compliance Committee, the CRO will build the enterprise-wide risk governance framework that defines the Bank's risk culture, appetite, and limits, and will own the ongoing monitoring of these risks and of operational performance to ensure alignment with Board-approved policies and tolerances.

The CRO is a Bank-only executive with no concurrent Sezzle Inc. position and reports to the President of Sezzle Bank and to the Board Risk and Compliance Committee.

What You'll Do:

Risk Governance & Framework

• Define enterprise-wide risk management strategies, policies, and the risk appetite framework; work with the Board and the Board Risk and Compliance Committee to establish the Bank's risk culture, appetite, and limits.
• Identify, assess, measure, manage, monitor, and report on risk across the Bank, and ensure compliance with Board-approved policies, tolerances, and risk limits.
• Identify emerging areas of risk, including potential risks associated with proposed new products and services, and ensure business strategies align with regulatory rules, guidance, and supervisory expectations.
• Develop and maintain a model governance framework that includes independent model validation.
• Participate in ALCO as the independent second-line risk perspective.

Regulatory & Examination Relationship

• Serve as the Bank's primary relationship manager for the OCC Examiner-in-Charge, coordinating with the Bank's President.
• Communicate with regulators and address regulatory inquiries and examination activities.
• Serve as the Bank's designated CRA Officer: administer the CRA Strategic Plan, monitor the Bank's progress against its CRA performance commitments, and ensure CRA examination readiness.

Second-Line Oversight

• Oversee the Bank's Chief Compliance Officer and the second-line compliance risk management function, including complaints handling and emerging regulatory and consumer compliance requirements.
• Oversee the Bank's BSA Officer; ensure BSA/AML/OFAC policies, procedures, risk assessments, and controls are properly designed and operationally effective.
• Oversee the Bank's Chief Information Security Officer (CISO) to ensure information assets, sensitive customer data, and technologies are protected; ensure the CISO reports routinely to the Board or the appropriate Board committee.

Board & Business Partnership

• Serve as the primary source for all risk program communication and reporting to the Board and the Board Risk and Compliance Committee.
• Develop and maintain strong relationships with business line management, effectively communicating emerging and present risk elements and issues.
• Provide support and insight to the Bank's audit program, including addressing audit findings and remediation efforts.

What We Look For:

• 15–20+ years of banking or financial services experience, with significant time in risk management, credit, compliance, or audit.
• Minimum 7–10 years in a senior risk leadership role (CRO, SVP Risk, or equivalent) at a regulated financial institution.
• Extensive experience managing a risk organization in a regulated banking environment, including direct experience with federal banking regulators (OCC, FDIC, or Federal Reserve) and the examination process.
• Deep knowledge of enterprise risk management frameworks, banking regulatory requirements, and second-line governance.
• Experience managing compliance, BSA/AML, OFAC, CRA, and cybersecurity risk programs.
• Strong communication skills with Board-level risk reporting experience.
• Demonstrated experience working with Claude or equivalent large language model tools is required; candidates must be comfortable leveraging AI to enhance productivity, research, and communication.

Preferred Qualifications:

• Bachelor's degree in Finance, Economics, Accounting, or Mathematics; Master's degree preferred.
• FRM (GARP), CERP (ABA), CAMS, CRCM, or CPA certification highly valued.
• Experience with model risk governance and CECL/stress testing frameworks.
• Prior experience with de novo bank formation or building a second-line risk function from the ground up.

About You:

• You exhibit strong character. You do what you say you'll do and you do the right thing, even when no one is watching. You're a strong team member and secure enough to give others credit.
• You communicate openly and honestly. You listen well, speak candidly, and stay open-minded. You hold yourself accountable, and when you disagree with a decision, you say so respectfully. Once the call is made, you commit fully.
• You act like an owner. You put customers, merchants, and shareholders at the center of what you do. You bring solutions, not just problems. You seek out responsibility, work hard and smart, and move quickly, knowing that most decisions can be reversed.
• You get things done. You're a doer, not just a planner. No task is beneath you, and you're always willing to roll up your sleeves and dig in. You take work from idea to finished, and you don't wait for someone else to pick up the slack.
• You're driven to succeed. You're passionate, tenacious, and competitive. You hold yourself and others to a high bar, fix problems so they stay fixed, and keep going through setbacks.
• You have fun. You enjoy working with your teammates, keep a sense of humor, and keep work issues in perspective.

What Makes Working at Sezzle Awesome:

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire.

Compensation:

Compensation is market-competitive and commensurate with experience. Specific compensation offered to a candidate will be dependent on factors such as education, experience, qualifications, and alignment with market data.

Perks & Benefits:

• Unlimited PTO, volunteer hours and sabbatical
• Life, STD/LTD, medical, dental and vision insurance
• Highly discounted LifeTime gym membership
• 401k with match
• Collaborative fun co-workers
• The opportunity to join the fastest growing FinTech alongside a team of motivated and driven individuals

 

Sezzle's Employee Privacy Policy:

At Sezzle, we care about protecting your personal information. When you apply for a position with us, any data you share as part of the application process is handled in accordance with our Employee Privacy Policy, which also covers applicants. We encourage you to review it to understand how your information is collected, used, and safeguarded. You can read the full policy here: https://legal.sezzle.com/state-employee-privacy-policy.

CCPA Disclosure:

Sezzle Inc. is committed to protecting the privacy of our job applicants. In compliance with the California Consumer Privacy Act (CCPA), we inform California residents about the personal information we may collect, the purposes for its collection, and your rights under the CCPA. For details about the categories of personal information we collect and your rights under the CCPA, please visit Sezzle's Employee Privacy Policy: https://legal.sezzle.com/state-employee-privacy-policy. By submitting your application, you acknowledge that you have read and understood this CCPA disclosure.

Equal Employment Opportunity:

Sezzle Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, national origin, age, disability, genetic information, pregnancy, or any other legally protected status. Sezzle recognizes and values the importance of diversity and inclusion in enriching the employment experience of its employees and in supporting our mission.

To apply: https://weworkremotely.com/remote-jobs/sezzle-chief-risk-officer

About Customer.io Over 9,000 companies — from scrappy startups to global brands — use our platform to send billions of emails, push notifications, in-app messages, and SMS every day. Customer.io...

Who We Are:SmithRx is a rapidly growing, venture-backed Health-Tech company.

Headquarters: United States
URL: https://engine.com/

About the Role

We're looking for a VP, Finance to lead Finance at Engine and serve as a strategic partner to our CEO and executive leadership team. 

You'll own the financial strategy and operating cadence of the company, from planning and forecasting to capital allocation, business performance, financial reporting, and long-range strategy. You'll help leadership understand what is driving the business, where we should invest, and what we need to do next. You'll also be the architect of Engine's financial story, shaping how the company is understood by its Board, investors, and partners.

You'll build the Finance organization and infrastructure to support Engine through its next phase of growth. That means creating clarity where there is ambiguity, building scalable processes before they become bottlenecks, and using data, systems, and AI to make Finance increasingly leveraged.

Success in this role will be measured by business impact and the results of the Finance organization.

What You'll Do

Strategic Financial Leadership

• Serve as the CEO's financial thought partner on growth strategy, investment priorities, resource allocation, and profitability. Drive capital allocation decisions across the executive team — where Engine invests people, capital, and resources, and where we make tradeoffs. Bring financial rigor to pricing, monetization, new products, markets, and partnerships.

Capital Strategy & Transactions

• Own fundraising, debt and liquidity strategy, M&A, and other strategic transactions. Build investor relationships, lead the Board story on performance, and prepare Engine for future capital events — including the reporting, controls, and governance a public-ready company requires (SOX readiness, audit committee partnership, external guidance frameworks).

Financial Planning & Business Insight

• Own the financial plan — quarterly forecasting, long-range modeling, scenario analysis, and the operating cadence across Engine. Develop a deep understanding of revenue, margins, customer economics, pricing, payment economics, and cash flow. Build the metrics and frameworks that make the business legible to leadership.

Narrative & Communication

• Tell Engine's financial story to the Board, investors, lenders, and partners — turning complex numbers into a narrative leadership can act on and external audiences believe. Lead financial reporting and help the CEO communicate performance, outlook, risks, opportunities, and key decisions with clarity.

Build Finance for Scale

• Build and lead a high-performance Finance team — attracting exceptional talent, modernizing through AI and automation, and establishing systems, processes, data infrastructure, and controls that scale without creating bureaucracy. Partner with Accounting, Treasury, Legal, and external advisors to ensure Engine has the financial foundation required to scale responsibly.

What You'll Bring

Experience and Background

• 12+ years of experience across investment banking, private equity, growth equity, corporate finance, FP&A, strategic finance, or a related field, with significant experience in high-growth technology.
• Investment banking or private equity background, with hands-on experience in valuation, transaction execution, and capital markets. Strongly preferred.
• Experience leading Finance, or a major component of Finance, at a high-growth tech, SaaS, marketplace, fintech, or similarly complex company.

Financial Expertise

• Exceptional financial modeling skills and a strong understanding of three-statement modeling, unit economics, cash flow, and capital allocation.
• A track record of building financial planning, forecasting, reporting, and analytical infrastructure in environments that are scaling quickly.
• Experience evaluating pricing, monetization, new products, investments, headcount, and other strategic decisions.

Communication and Partnership

• A track record of communicating complex financial stories to investors, boards, and executive teams in ways that drive decisions and build confidence.
• Experience partnering directly with a CEO, executive team, and Board.

Leadership and Team Building

• Experience building and developing high-performing Finance teams. Comfort operating without a fully defined playbook and  building structure where it doesn’t exist.

Judgment and Execution

• Strong commercial instincts. You understand that Finance exists to help the business make better decisions, not simply to explain what happened last quarter.
• The ability to operate at both the strategic and tactical level and an usually high bar for execution and bias towards action
• Strong conviction and judgment. You bring a point of view vs just presenting options.

Compensation
Our compensation packages are based on several factors, including your experience, expertise, and location. In addition to a competitive base salary, all roles receive equity. Depending on the role, total compensation may also include an annual bonus. Your recruiter will share your complete compensation package as you move through the process.

Base Pay Range

$300,000 - $375,000 USD

The Engine Edge: Perks & Compensation
We believe in rewarding great work with great benefits:

• Compensation: Competitive base pay tied to role and experience, with equity for all employees. Some roles are also eligible for bonuses or commissions.
• Benefits: Check out our full list at engine.com/culture 
• Environments for Success: Different roles have different needs in terms of the environments that drive success which is why we have a hybrid-hub model. Whether you are in one of our amazing offices or fully remote, we'll make sure you have what you need to succeed.

Perks and benefits may vary based on employment type, location, and more

To apply: https://weworkremotely.com/remote-jobs/engine-vp-finance

At Mitel, you will have the opportunity to help businesses connect, collaborate and provide better experiences for our customers.

Are You Ready? CAI is a professional services company established in 1996 that has grown year over year to nearly 800 people worldwide. For mission-critical and regulated industries that need...

COMPANY OVERVIEW: Unison is a leading telecom and renewables infrastructure investment firm founded in 2003 that has successfully invested more than $2 billion in acquiring assets in the U.S. and...

Headquarters: NY, United States
URL: https://www.cloverhealth.com/

Chief Actuary

Remote - USA

The Finance team at Clover Health is a group of strategic partners providing financial and operational insights that drive informed decision-making and efficient capital allocation. Guided by our core values of excellence, accountability, and collaboration, we provide actionable recommendations to improve health outcomes and reduce costs while ensuring financial integrity and innovation.

Actuarial is at the center of some of Clover's most important decisions—from pricing and forecasting to reserving, medical economics, and long-term strategy. As Chief Actuary, you'll lead and evolve this function during a pivotal stage of the company's growth, helping shape how we deploy AI, automation, and advanced analytics to improve decision-making across the business.

This isn't a traditional Chief Actuary role. We're looking for someone who can combine deep actuarial expertise with modern technology, building AI-enabled workflows that transform how actuarial work gets done while maintaining the rigor, transparency, and governance required in a highly regulated environment. You'll partner closely with leaders across Finance, Clinical, Growth, Operations, and Product to influence company strategy while building a best-in-class actuarial organization.

As a Chief Actuary, you will:

• Lead Clover's enterprise actuarial function, including pricing, forecasting, reserving, medical economics, Part D, Stars analytics, and bid strategy.
• Establish the long-term vision for actuarial, modernizing the function through AI, automation, and scalable analytical infrastructure. 
•  Build AI-enabled workflows that reduce manual effort, accelerate insight generation, and improve actuarial decision-making while ensuring explainability, governance, and regulatory compliance.
• Lead the annual Medicare Advantage bid strategy and pricing process, framing tradeoffs among growth, competitiveness, margin, risk, and capital requirements to support enterprise planning and executive decision-making.
• Assume responsibility for actuarial opinions, reserve adequacy, and related regulatory actuarial requirements, including transitioning responsibilities currently supported by external actuarial partners.
• Guide reserving methodology, IBNR development, forecasting, and emerging experience analysis to provide timely, reliable financial insights.
• Partner with Finance leadership to strengthen forecasting, planning, capital management, and enterprise performance measurement.
• Collaborate with Medical Economics to identify healthcare cost trends, evaluate interventions, and develop strategies that improve member outcomes while managing medical expense. 
•  Drive adoption of modern analytics tools and AI capabilities across the actuarial organization, helping the team operate faster, smarter, and with greater transparency.
• Serve as a trusted advisor to executive leadership, translating complex actuarial concepts into clear business recommendations. 
• Lead, develop, and scale a high-performing actuarial organization, including organizational design, performance management, workforce capacity, and development of actuarial and analytical talent.
• Build strong partnerships across Finance, Clinical, Operations, Growth, Data Science, and Engineering to ensure actuarial insights are embedded in strategic decision-making.
• Establish and maintain actuarial governance, model review, documentation, control, and validation standards that support regulatory compliance, financial integrity, and sound executive decision-making.

Success in this role looks like:

First 90 Days

• Build trusted relationships across Finance and key business partners. 
•  Assess the current actuarial organization, tools, and operating model.
• Develop a roadmap for AI adoption and workflow automation across the actuarial function.
• Gain deep familiarity with Clover's pricing, forecasting, reserving, and medical economics processes.

First 6 Months

• Begin implementing AI-enabled actuarial workflows that improve efficiency and insight generation.
• Strengthen forecasting, reserving, and bid processes through improved automation and cross-functional collaboration.
• Successfully assume ownership of additional actuarial responsibilities, including reserve oversight and governance.
• Establish a clear long-term organizational vision for the actuarial function.

Long Term

• Build one of the industry's most modern actuarial organizations by combining deep actuarial science with AI-enabled decision support.
• Improve forecasting accuracy, operational efficiency, and enterprise decision-making through advanced analytics and automation.
• Develop a highly engaged, high-performing actuarial team that is recognized as a strategic partner across the organization.

You should get in touch if:

• You are a Fellow of the Society of Actuaries (FSA) and a Member of the American Academy of Actuaries.
• You have significant leadership experience in Medicare Advantage actuarial functions, including pricing, reserving, forecasting, and bid development.
• You are an AI evangelist and have demonstrated experience deploying AI workflows across your functional areas. Moreover, you are enthusiastic about applying automation and modern tooling to fundamentally improve the actuarial function.
• You have experience leading large, cross-functional initiatives that influence executive decision-making.
• You are equally comfortable discussing actuarial methodology with technical experts and communicating business implications to executives and non-technical stakeholders. 
• You have a track record of building, mentoring, and developing high-performing actuarial teams.
• You thrive in fast-moving environments where you can build, innovate, and shape the future of an organization.

Benefits Overview:  

• Financial Well-Being: Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program, 401k matching, and regular compensation reviews to recognize and reward exceptional contributions.
• Physical Well-Being: We prioritize the health and well-being of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health matters to us, and we invest in ensuring you have access to quality healthcare.
• Mental Well-Being: We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous flexible time-off policy. Additionally, we embrace a remote-first culture that supports collaboration and flexibility, allowing our team members to thrive from any location. 
• Professional Development: Developing internal talent is a priority for Clover. We offer learning programs, mentorship, professional development funding, and regular performance feedback and reviews.

Additional Perks:

• Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities
• Reimbursement for office setup expenses
• Monthly cell phone & internet stipend
• Remote-first culture, enabling collaboration with global teams
• Paid parental leave for all new parents
• And much more!

About Clover: We are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we've created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most.

We always put our members first, and our success as a team is measured by the quality of life of the people we serve. Those who work at Clover are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare.

From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone's responsibility.

#LI-REMOTE

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are an E-Verify company.

Final pay is based on several factors including but not limited to internal equity, market data, and the applicant’s education, work experience, certifications, etc.

A reasonable estimate of the base salary range for this role is:

$274,000 - $356,000 USD

To apply: https://weworkremotely.com/remote-jobs/clover-health-chief-actuary

The Finance team at Clover Health is a group of strategic partners providing financial and operational insights that drive informed decision-making and efficient capital allocation. Guided by our core values...