About the Role

Fivetran is building data pipelines to power the modern data stack for thousands of companies. The Enterprise Account Executive will drive towards aggressive new customer and partner revenue goals, while growing our footprint in the Enterprise market.

This is a full-time, remote position and must be based out of the US in NJ, NY, CT or PA. 

What You’ll Do

• Collaborate cross-functionally with marketing, customer success, alliances, operations, and analytics to drive pipeline generation and exceed revenue goals.

• Accelerate the growth & adoption of Fivetran in the Enterprise Market through value-driven sales cycles.

• Lead in-depth discovery and demonstrate a deep interest in our Enterprise customers’ data challenges, identify required capabilities and positive business outcomes to drive towards valuable long term customer engagements.

• Speak comfortably about Fivetran’s vision to a broad range of audiences from C-level executives to individual contributors.

• Seek out and land deals with new Enterprise target accounts, then look to grow their footprint with Fivetran through new use cases, cross-sells and expansion.

• Build strategic relationships with partners in order to identify new opportunities and accelerate deal cycles.

• Forecast accurately and provide clear visibility on sales and revenue performance by actively managing and progressing opportunities.

Skills We’re Looking For

• 8+ years of large enterprise software sales experience and well-developed pattern recognition for navigating complex organizations.

• Excellent written and verbal communication skills, with the ability to hold multiple stakeholders accountable throughout a complex value-driven sales cycle.

• In-depth familiarity with the modern data technology industry and key players.

• You are familiar with a solution-based approach to selling, have experience managing a complex sales process and possess excellent presentation and listening skills, organization and contact management capabilities.

• You thrive in an extremely fast-paced, ever changing work environment.

• You’re able to keep up with a highly motivated team in a market that is growing extremely fast.

• You are extremely organized.

• You are able to juggle lots of things at once while not letting anything drop.

• You are a strategic thinker.

• You are able to see and communicate the big picture in an inspiring way. You are a problem solver.

• You are resilient and creative, able to be resourceful to proactively seek out a solution to a problem.

This position qualifies for Fivetran’s incentive plan, and it’s common for employees in this role to achieve the total on-target earnings.

As part of our commitment to setting new hires up for success, all new sales team members attend a one-week, in-person Revenue Bootcamp during their second week at Fivetran. This bootcamp, held at one of our designated company locations, requires travel and is a mandatory part of the onboarding process.

#LI-REMOTE #LI-MP1

About the Role

Fivetran is building data pipelines to power the modern data stack for thousands of companies. We’re looking for a Regional Director, Enterprise Sales to lead and scale a team of high-achieving, high-integrity Enterprise Account Executives focused on driving new business and expansion opportunities across Fivetran’s most strategic accounts. This role reports directly to the RVP of Enterprise Sales and will be a foundational leader in our Enterprise business.

This is a full-time, remote position and must be based out of NJ, NY, CT, or MA in the United States.

What You’ll Do

• Attract, hire, develop, and empower a team of Enterprise Account Executives to consistently and predictably exceed Fivetran’s growing Enterprise revenue targets

• Drive a high-accountability culture through best-in-class coaching, modeling clear expectations for achievement, and evangelizing a disciplined process for the team

• Champion outstanding sales rigor through value-based Command of the Message and MEDDPICC methodologies

• Collaborate cross-functionally with leaders in Marketing, Customer Success, Alliances, Product, and Revenue Operations to build an effective

• Enterprise GTM motion Collaborate externally with our incredible ecosystem of partners including SI’s, GSI’s, and tech partners

• Ensure excellence in sales execution for complex multi-stakeholder deals while building the foundation for growth in enterprise accounts

• Drive AE-ownership of Enterprise pipeline generation and encourage effective AE/BDR collaboration to efficiently prospect, identify, qualify and build sustainable pipeline

• Forecast clearly to the executive leadership team, with consistent accuracy and a deep knowledge of the Enterprise business

• Work in lockstep with our technology and SI partners to achieve a successful co-selling motion 

Skills We’re Looking For

• 5+ years enterprise sales leadership experience with a consistent track record of recruiting and retaining high-performing senior AEs selling a technical solution to large, complex enterprises

• Proven and repeatable history of overachievement both as an enterprise seller and a leader whose teams consistently exceeded revenue targets and accelerated their careers under your leadership

• Natural ability to lead and motivate AEs through continuous growth and change; easily able to earn the trust and respect of the team with a One Team One Dream mindset Passion for field sales — a leader who can’t wait to jump into deals, connect directly with Economic

• Buyers, and provide the air coverage and executive bridging needed to close new and expansion opportunities with Enterprise companies.

• This includes working with reps and prospects/customers/partners face to face wherever possible

• Experience partnering cross-functionally and co-selling with external partners to build an Enterprise business from the ground up

• Expertise in both land and expand sales motions, an insatiable curiosity about our customers, and a data-backed vision for how Fivetran can drive positive business outcomes in the Enterprise business

• Experience building and championing an outbound selling culture and driving accountability for qualified pipeline generation Unwillingness to settle for good results when great results are possible 

Bonus Skills​

• Experience with a consumption business is a plus!

• Demonstrated ability to leverage the power of AI to drive a richer, more robust sales motion.

This position qualifies for Fivetran’s incentive plan, and it’s common for employees in this role to achieve the total on-target earnings.

As part of our commitment to setting new hires up for success, all new sales team members attend a one-week, in-person Revenue Bootcamp during their second week at Fivetran. This bootcamp, held at one of our designated company locations, requires travel and is a mandatory part of the onboarding process.

#LI-REMOTE #LI-MP1

Hi, we're Oscar. We're hiring a Senior Manager, Technical Accounting to join our Accounting team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

Senior Manager, Technical Accounting, would lead our technical accounting work. You will work cross-functionally to understand and to provide technical accounting guidance on new or complex transactions and corresponding financial disclosures. You will develop, enhance, and maintain accounting policies and ensure policies reflect current practices and operations of the business and are up-to-date and compliant with existing and newly adopted accounting standards and regulations.

You will report into the Associate Director, SEC Reporting and Technical Accounting.

Work Location: 

This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $134,136 - $176,053 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Lead our technical accounting work required under US GAAP and statutory reporting and partner with the Tax Team to ensure tax aspects are considered.
• Partner with teams, and external partners and/or consultants, to:
  • provide technical accounting expertise to support new transactions and new or evolving business arrangements, and
  • prepare technical accounting analysis on complex accounting issues.
• Create our accounting policies.
• Oversee, and apply new accounting pronouncements applicable to the Company.
• Work with the Company's external auditors on technical accounting matters.
• Help review financial disclosures in SEC and statutory filings related to our accounting policies and impact of new accounting pronouncements.
• Develop relationships with cross-functional teams to understand broad goals and provide accounting guidance and best practice recommendations to allow process improvements.
• Perform ad-hoc technical accounting research and analysis to support special projects.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• 6+ years of relevant experience.
• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• Certified Public Accountant licensure (CPA).
• 2+ years of experience with US-based insurance companies.
• 2+ years of practical experience in financial reporting.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience working collaboratively across the organization.
• 4+ years of experience with US-based insurance companies.
• 4+ years of practical experience in financial reporting.
• 6+ year in public accounting

Hi, we're Oscar. We're hiring a Senior Accountant, Statutory and Legal Entity Reporting to join our Finance Ops & Accounting.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Financial Reporting is responsible for execution of statutory legal entity reports. This includes the preparation of statutory financial exhibits and footnotes, analytics, audited financial statements and supplemental filings.

You will report into the Associate Director, Financial Reporting.

Work Location: This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $82,717 - $108,566 per year.You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Monthly, quarterly and annual financial reporting
  • Completing the monthly, quarterly, and annual statutory (and stand-alone legal entity) reporting processes, including analytics and related financial statement disclosures.
  • Executing work related to the statutory audit efforts.
• Work on process improvement opportunities.
• Work with Regulatory Relations and other teams across the Organization to respond timely to regulator inquiries.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in Accounting, Finance, or related field, or 4 years of relevant experience.
• 3+ years of related experience on an accounting or reporting team.

Bonus points:

• Experience in a similar position at a health insurance company.
• Experience with US-based insurance companies.
• Certified Public Accountant licensure (CPA).
• Practical experience in statutory reporting.

Hi, we're Oscar. We're hiring a Manager to join our Treasury organization.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Treasury Manager is an individual contributor responsible for managing Oscar Health's important treasury operations and daily liquidity. You will provide critical daily execution of cash management activities, optimizes cash usage across subsidiaries, and guides operational efficiencies in banking and treasury systems.

The Manager will be a critical partner to the Treasury organization, driving the execution of cash management strategies in a capital-intensive insurance environment. You have a deep, operational understanding of Treasury practices.

You will report into the Senior Director, Assistant Treasurer.

Work Location: This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $108,000 - $141,750 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Liquidity Management & Optimization: Recommend and monitor minimum cash balances required at subsidiaries, based on forecasts from the Capital Planning team, to ensure safety and liquidity while optimizing excess cash for investment. Guide the efficient use of cash across the Parent and Subsidiaries.
• Cash Flow Reporting & Forecasting: Responsible for updating actual cash flows for each subsidiary and synchronizing with the Capital Planning team to ensure forecasted outflows are current. Updated cash forecasts and variances to the broader finance team.
• Reconciliation and Performance Analysis: Reconcile actual cash balances reported from Accounting with Treasury forecasts to true-up balances. Describe actual versus forecast variances, and update Net Investment Income (NII) actuals related to cash and short-term holdings.
• Operational Oversight & Execution: Build all critical treasury operations and daily banking activities. This includes ensuring accurate daily funds settlement, bank account maintenance, processing signatory updates, and the administration of bank portal systems (e.g., CashPro, JPM Access, WF Vantage).
• Risk & Fee Analysis: Measure banking service fees paid to financial institutions. Analyze counterparty risk exposures related to cash and bank balances.
• Operational Efficiency & Projects: Assist with project management, process improvement programs (e.g., RFPs, accounts/services rationalization), and implementing technology to enhance cash management and reporting functions.
• Audit and Compliance Support: Provide comprehensive operational support for all internal and external audits, SOX compliance controls, and state regulatory examinations, ensuring all processes are documented.
• Banking Relations: Serve as an important operational interface with external banking partners to resolve daily issues, manage service levels, and support routine operational tasks.
• Record Management and Governance: Responsible for managing all official records and documentation for Treasury Operations (e.g., debt indentures, banking agreements, fee invoices) within the shared file structure. Manage the Treasury Calendar of Events to track critical due dates for reports, payments, compliance filings, and renewals.

Requirements:

• Experience: 5+ years of progressive, hands-on experience in Corporate Treasury, Cash Management, or Treasury Operations within the financial services or insurance industry.
• Functional Expertise: 3+ years directly managing corporate liquidity, daily cash positioning, and detailed cash flow reporting/forecasting processes.
• Operational Systems: Operational experience using major online bank portals (e.g., CashPro, JPM Access, WF Vantage) and managing daily fund movements and settlements.
• Communication & Theory: Strong communication and presentation skills with the ability to articulate financial concepts. Must understand core Treasury Operations and cash management principle
• Education: Bachelor's degree in Finance, Accounting, Economics, or a related quantitative field.

Bonus points:

• Prior experience in Treasury Operations within an insurance or healthcare company.
• MBA and/or CTP certification is preferred. 
• Experience with ERP systems (e.g., Workday) and investment accounting/reporting systems (e.g., Clearwater) for data extraction and analysis; proficiency with Google Suite (Sheets, Docs, Drive) for collaboration and record management is a plus.

Hi, we're Oscar. We're hiring an Associate Director, Tax to join our Finance.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate Director, Tax leads income tax compliance including tax provisions under Generally Accepted Accounting principles (GAAP) and Statutory reporting, federal, state and local tax returns, and tax planning and projects. The Associate Director, Tax supports the Tax leadership team in developing department strategy.

You will report into the Sr. Director, Tax.

Work Location: 

This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $180,504 - $236,911 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Manage the annual and quarterly tax GAAP and Statutory tax provision processes and lead the related internal and external relationships necessary to support these processes.
• Review U.S. federal, state, and local tax returns and estimates for the corporate holding companies and insurance subsidiaries and manage our relationship with external consultants on this work.
• Ensure integrity of tax accounting and compliance results using technology solutions, partnering with the Finance Transformation Team and the Company's external vendors.
• Manage tax responses to audits and notices and the related correspondence with internal and external parties.
• Ensure compliance with indirect tax compliance functions.
• Lead the preparation of financial data and analysis to support tax forecasting and projects.
• Partner with areas of Finance and the business to address tax issues and meet organizational goals.
• Stay abreast and educate others on developments within the insurance tax area and their possible effects to the Company.
• Help develop and implement tax strategies and planning opportunities.
• Automate processes to refine tax compliance and provide analytical insights.
• Compliance with all applicable laws and regulations.
• Other duties as assigned.

Requirements:

• Bachelor's degree in Accounting, or 4 years commensurate experience.
• 7+ years of tax experience in a public accounting firm or equivalent experience in a corporate tax department.
• Proficient in using code and regulations.
• Strong knowledge in ASC 740.
• 3+ years experience as a team leader.

Bonus points:

• CPA and/or Master's of Taxation.
• Statement of Statutory Accounting Principle (SSAP) 101 reporting.
• Knowledge of domestic tax issues affecting U.S. insurance companies.
• Experience implementing tax provision software.
• Work with large datasets to build models and leverage tools.
• Experience with state tax nexus considerations.

Hi, we're Oscar. We're hiring an Associate, Medical Economics to join our Medical Economics team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Associate, Medical Economics, is part of our Medical Cost Analytics team within the Medical Economics department. The Associate reports to the Senior Director, Medical Economics, and is part of a team that analyzes medical costs to understand trend drivers, project financial outcomes, monitor programs, and identify cost savings opportunities. You will partner with Medical Economics leadership, Data Science, Finance, Payment Integrity, and other analytic support responsibilities to ensure accurate projections are reflected in management reporting.

You will report into the Senior Director, Medical Economics.

Work Location: 

This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $123,372 - $161,925 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Work under the guidance of the Senior Director, Medical Economics.
• Maintain sophisticated models to forecast the financial impact of proposed changes to clinical and payment policies. Conduct sensitivity analyses and stress testing on models to understand the range of potential outcomes under multiple utilization and cost scenarios.
• Develop knowledge of industry best practices and work to drive innovation.
• Perform in-depth analysis of integrated claims and operational data (medical, pharmacy, lab, auths) to identify cost and trend drivers.
• Provide proactive financial guidance on latest clinical trends and their potential impact on our financial performance.
• Accomplish retrospective studies to measure the actual financial and clinical outcomes of implemented policies, comparing results against initial projections.
• Build repeatable analytic processes that scale across programs.
• Create executive-ready visualizations tailored to different stakeholder audiences (clinical vs. financial).
• Promote and shape Oscar best practices concerning automation and documentation. Contribute to department initiatives around automation, AI use, and tooling improvements.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• College degree in a STEM field: e.g. Economics, Actuarial Science, Health Economics, Biostatistics, Health Informatics, Health Services Research.
• 4+ years of quantitative analysis experience using SQL.
• Demonstrable track record of building analytics that drive business decisions and actions.

Bonus points:

• Associate or Fellow of the Society of Actuaries (SOA), or on the track to become one.
• Excellent communication, collaboration, and relationship-building skills.

Hi, we're Oscar. We're hiring an Analyst II, Actuarial to join our Actuarial.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Analyst II, Actuarial maintains Oscar's forecasting, valuation, and pricing processes for several Affordable Care Act (ACA) markets. You will oversee regularly maintaining and reviewing actuarial models used to develop pricing, forecasting, trend analytics, Incurred but not Reported (IBNR) projections and risk adjustment accruals.

You will report into the Manager, Actuarial.

Work Location: This is a remote position, open to candidates who reside in: Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $72,800 - $95,500 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Maintain core pricing and plan design models. Ensure consistency and standardization across team users.
• Important contributor in developing and submitting regulatory filings, and developing a viewpoint and recommendation for strategic pricing decisions.
• Develop and provide recommendations for the accrual setting process with respect to IBNR claims, Risk adjustment and Shared Savings deals.
• Identify and triages meaningful observations of experience across plan designs, providers, vendors, and markets.
• Promote and shape Oscar actuarial best practices concerning automation and documentation.
• Maintain relationships, rapport, and lines of communication with all partners.
• Aid in the onboarding of analysts by collaborating and integrating them into existing processes.
• Compliance with all applicable laws and regulations
• Other duties as assigned

Requirements:

• Bachelor's degree in a STEM field.
• Passed a minimum of two actuarial exams.
• 2+ years of experience in a related field.

Bonus points:

• Experience with health insurance concepts and nuances.
• Highly technical with a strong enthusiasm to apply tech-forward methods in actuarial models.
• Proficient in coding

Hi, we're Oscar. We're hiring a Senior Actuarial Analyst to join our Actuarial team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role:

The Senior Analyst, Actuarial will play a key role in Oscar’s valuation function, focusing specifically on risk adjustment across all Affordable Care Act (ACA) markets. This role will own the maintenance and review of actuarial models used to develop risk adjustment accrual estimates, forecasting estimates, and various other analyses.  This is a very dynamic space, which makes this a great opportunity to work on interesting projects and have a BIG impact.

You will report into the Director, Actuarial.

Work Location: This is a remote position, open to candidates who reside in:  Hartford, CT. You will be fully remote; however, our approach to work may adapt over time. Future models could potentially involve a hybrid presence at the hub office associated with your metro area. #LI-Remote

Pay Transparency: The base pay for this role is: $101,844 - $133,670 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities:

• Model Management: Maintain and enhance core risk adjustment reporting and forecasting models, ensuring consistency and standardization across all team users.
• Infrastructure & Design: Serve as a key contributor in improving modeling infrastructure; develop recommendations for model design decisions, best practices, and automation/documentation standards.
• Financial Strategy: Develop recommendations for the risk adjustment accrual setting process and provide data-driven insights for the financial planning process.
• Trend Analysis: Identify, triage, and investigate core drivers of observed trends across plan designs, providers, vendors, and markets.
• Stakeholder Engagement: Maintain strong relationships and clear lines of communication with internal and external stakeholders.
• Team Development: Aid in the onboarding of new analysts by collaborating and integrating them into existing processes.
• Governance: Compliance with all applicable laws and regulations.
• Other duties as assigned.
•  

Requirements:

• Bachelor's degree in a STEM field.
• Associate or Fellow of the Society of Actuaries (SOA), or on the track to become one.
• 3+ years of experience in a related field.

Bonus points:

• Strong knowledge of core health insurance concepts and experience with actuarial applications.
• Highly technical with a strong enthusiasm to apply tech-forward methods in actuarial models.