Tremendous is the global platform built for businesses to send thousands of payouts to anyone, anywhere, for free. Recipients can choose from 2,500+ reward options they’ll love: gift cards, prepaid cards, bank transfers, and more. If they have issues, we handle them so teams don’t have to. And we track what's been sent and spent along the way.

Tremendous

Health Insurance

Equity / Stock Options

Unlimited PTO

Paid Parental Leave

Tremendous is the global platform built for businesses to send thousands of payouts to anyone, anywhere, for free. We're trusted by 20,000 organizations like Atlassian, MIT, and United Way to deliver gift cards and money to millions of recipients worldwide.

Our customers (researchers, marketers, HR teams, nonprofits, and platform businesses) rave about how fast and easy Tremendous is to use. 

Tremendous is profitable and growing without outside investors. We’re a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life. The team agrees– our employee NPS is in the high 80s.

We're hiring a Senior Product Manager for our AI Enablement team. This team has one mission: make everyone at Tremendous faster by making AI accessible, reliable, and secure across the company. It builds Rockie (our internal AI agent that debugs issues, runs data analyses, and writes code), internal automations for teams like finance and support, and the infrastructure that makes AI safe to use company-wide.

This is not a typical PM role. You'll own the internal AI product surface end to end: finding the workflows worth automating, mapping how they actually work, and turning them into working prototypes that our engineers then build into production systems. You'll report to our co-founder / Head of Product and work with a team of fast-moving engineers.

 Sit with finance, sales, support, and ops. Map their workflows. Find the automations and agents worth building, and prioritize by business impact.

 You'll build working versions of agents and automations with AI tools (Claude, Cursor, agent frameworks), because a working prototype is the best requirements doc.

Turn prototypes into specs engineers can build from.

 You keep a pipeline of well-defined, shovel-ready work so the team always knows what to build next and why.

 Define what "working correctly" means for each automation: evals, guardrails, edge cases, and observability.

 You'll do the PM work too: clear blockers, make scope calls, and keep projects moving through the build phase.

 An automation nobody uses is a failed project. You'll roll out what we build and iterate with the teams whose work changes.

 Define where Rockie and our internal agents go as internal AI grows from a team into a platform.

Professional software engineering experience. You've built and shipped production software, and you understand the security risks that come with giving AI systems access to real data and tools.

Experience owning a product end to end: as a technical founder, founding engineer, forward-deployed engineer, or PM. Formal PM experience is a nice to have, not a requirement.

Deep, hands-on AI experience. You've shipped LLM-powered systems and you build with AI tools daily. You understand agents, evals, and where models fail.

Business sense. You can sit with a finance or sales team, understand their process, and spot what's automatable (and what isn't).

A 0-to-1 track record. You've built products or tools from nothing.

Outstanding written communication. We're a documentation-first culture.

 You'll spend your days building agents and automations with cutting-edge AI tools, at a company that's fully bought in on AI.

 Base salary for this role: $225,000 to $300,000.

 100% covered health (US), unlimited PTO, 12-16 weeks paid parental leave.

Senior Level

AI Proficiency

Experience

Tremendous is seeking a Senior Product Manager for its AI Enablement team to build internal AI agents and automations. The role involves running discovery across the company, prototyping AI-powered workflows using tools like Claude and Cursor, and defining technical specifications for engineers. Candidates should have a background in software engineering and a proven track record of shipping LLM-powered systems.

Senior Product Manager - AI Enablement

Full Time

Tremendous is profitable and growing without outside investors. We're a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life. The team agrees– our employee NPS is in the high 80s.

We're looking for an Operations Analyst to join our small-but-mighty operations team. As the third person on the team, you'll shape how we handle day-to-day compliance operations and have real autonomy to drive impact. This role sits at the intersection of security, user experience, and sound judgment, requiring someone who doesn't just follow rules but thoughtfully balances risk, customer needs, and operational excellence.

Review account activity and make informed decisions using AI-assisted analysis. You'll investigate payment approval requests, flag anomalies through pattern recognition tools, and make sound judgment calls on approval or escalation, combining human judgment with AI insights.

Identify suspicious activity and fraud patterns. Learn about regulatory requirements as they come up and help implement them in your day-to-day work. Use AI tools to rapidly surface anomalies and patterns, freeing you to focus on the judgment calls that matter most.

Suggest process improvements that could make things more efficient or reduce risk. Document what you learn and share it with the team.

Balance compliance with user experience by using AI to process large datasets, draft communications, and analyze trade-offs at scale. Work cross-functionally with product, support, and business teams to make decisions that reduce risk and support scalable growth.

Strong analytical and problem-solving skills with exceptional attention to detail. You can take a messy situation, break it down, and see the pattern.

Familiarity with AI tools and a willingness to experiment with them for productivity. You don't need deep AI expertise, but you're comfortable learning to use LLMs, data analysis tools, or automation platforms to augment your work.

Clear communication and genuine collaboration. You work well across teams, explain complex topics simply, and aren't afraid to ask for context.

Comfort with multitasking, prioritization, and staying organized amid competing demands.

An ownership mindset and genuine curiosity. You take responsibility for outcomes, seek continuous improvement, and think about how decisions affect users.

At least 2 years in an operational, compliance, or related role. Startup or fintech experience is a plus; what matters more is your adaptability and hunger to grow.

 Base salary for this role: $95k to $105k.

Startup Experience

Tremendous is seeking an Operations Analyst to join its remote business operations team. The role focuses on managing day-to-day compliance operations, identifying fraud patterns, and utilizing AI tools to optimize risk management and user experience. The successful candidate will balance regulatory requirements with operational excellence to support scalable growth.

Operations Analyst

Competitive compensation

Remote Work

We're looking for a Sales Strategy & Operations Manager to be the business partner behind our sales organization. The role has two sides, and you'll own both.

The first is the operating machine: commissions, quota and attainment tracking, deal desk support, sales processes, and the weekly operating cadence with sales managers. Much of this is documented and increasingly automated. Your job is to run it reliably and keep making it smaller through automation.

The second is the work that machine makes room for: strategic analysis that changes decisions. Pipeline health diagnostics, rep capacity and quota modeling, segment performance, go-to-market experiments. Every analysis here ends in a recommendation, and you'll have a seat with sales leadership to see it through. Over time, you'll take on more of our target account strategy and how we build each AE's book of business.

You'll report to the Director of Revenue Operations and work daily with sales leadership.

Own the sales operating cadence: commissions (SDR monthly, AE quarterly), quota and attainment tracking, deal desk support, and the weekly sales manager meeting process

Deliver analyses that end in recommendations: pipeline health, conversion trends, capacity planning, segment performance - then partner with sales leadership to implement them

Grow into ownership of target account strategy and AE book-of-business planning

Automate your own job: we run an AI-forward stack (Cursor and Claude against Snowflake, HubSpot, and our BI tools), and we expect recurring work to shrink over time

Serve as connective tissue between Sales, Marketing, Product, Legal, and CS, including supporting sales enablement and onboarding programs

Push back constructively on sales leadership when the data disagrees

4-8 years in sales operations, revenue operations, strategy, or business operations at a B2B SaaS or fintech company

Strong analytical skills and a track record of turning data into recommendations that leadership acted on

Comfort with CRM systems (HubSpot a plus) and BI tools, plus genuine fluency with AI tools as part of your daily workflow

Experience running an operational process other people depend on (commissions, forecasting, deal desk, or similar)

Excellent stakeholder management across multiple functions at once

A bias toward action and an ownership mindset: you set your own direction and bring leadership along

You'll shape how a high-performing sales organization scales, influencing strategy, systems, and process design

You'll work directly with senior leaders across Sales, Marketing, and Product for high visibility and impact

You'll work at a company growing quickly yet sustainably. We're profitable with plenty more opportunity ahead

Competitive pay, equity and benefits. The base salary for this role is $135,000-$180,000

We're a remote company. Work from wherever you want in the Americas

Smart people and a great culture. See our 

SaaS

Stakeholder Management

Tremendous is hiring a Sales Strategy & Operations Manager to oversee the sales operating machine and deliver strategic analysis for leadership. Key responsibilities include managing commissions, quota tracking, and pipeline health diagnostics using an AI-forward stack featuring Snowflake, HubSpot, and BI tools. This is a fully remote role open to candidates across the Americas.

Sales Strategy & Operations Manager

Healthcare

We’re looking for a Senior PM to join our Platform team. This team owns infrastructure, security, and internal tooling that keeps every other team shipping.

Today, the product management org is six PMs, led by a co-founder who serves as Head of Product.

Report to our Co-founder / Head of Product, 

 This team is responsible for security issues, AI infrastructure, security improvements, data / compliance, and technical upgrades, and you’ll be involved in all of it.

 This is a highly technical product area that requires close collaboration with engineers and comfort discussing architecture, tradeoffs, implementation details, and complex technical problems.

 You’ll be working with stakeholders to help figure out what to build and when. When things are unclear, you'll resolve the ambiguity for the team.

 You’ll be expected to explain what problems we are solving and why. This helps our engineers and designers understand how to solve those problems.

 In order to frame those problems well, you’ll need to collect supporting evidence–from user interviews, market research, and competitive analysis.

Work with designers and engineers to devise solutions.

 PMs set requirements and then work with designers and engineers to select appropriate solutions.

 Tremendous has an async, non-meeting culture. This can be tricky if you're used to doing PM work in meetings.

 Not everyone will agree on priorities. It's the PM's job to drive decisions while keeping people in the process.

 Once we ship, you’ll be responsible for helping the team understand the impact of their work.

4+ years of PM experience on a platform team (infrastructure, platform, security, search, data, etc).

5+ years of professional software engineering or engineering management experience.

Exceptional technical fluency and problem-solving ability. You're comfortable discussing and solving complex technical problems with engineers.

Strong product intuition. You can look at a problem and see the right solution.

The ability to take a long-term strategy and a big feature backlog and translate that into roadmaps.

Outstanding written and verbal communication skills. We’re a documentation-first culture, and this role requires communicating effectively with senior stakeholders.

Comfortable making decisions without perfect information and moving work forward without being told to.

Genuine empathy for users and teammates. You want to understand their problems.

 Base salary for this role: $250,000 to $325,000.

Tremendous is seeking a Senior Product Manager for its Platform team to oversee infrastructure, security, and internal tooling. The role involves managing the product roadmap, collaborating with engineers on technical architecture, and driving decisions in an async, documentation-first environment. Candidates need extensive experience in platform PM and software engineering.

Senior Product Manager - Platform

We are hiring an experienced data analyst to partner with our internal stakeholders and help build the foundations that make AI-powered data access reliable.

You will support multiple business areas (including Product, Finance, and Customer Success) and contribute significantly to the semantic layer and our data model.

Tremendous values data as a first-class citizen and believes insights unlock significant growth. You will be an integral part of the data team and collaborate closely with company-wide stakeholders.

Contribute to trusted, reliable data models and semantic layer coverage that make AI-generated analyses more accurate.

Apply various analytics methods to gain insights into critical aspects of our business.

Consolidate diverse facts and findings into compelling narratives that can be applied across Tremendous.

Advocate for data-informed decisions by partnering with key stakeholders and senior leaders.

Identify and implement improvements within the Data team by standardizing processes, developing innovative practices, and fostering new expertise.

Join a growing data team and actively contribute to team collaboration and culture.

You write sophisticated SQL with a preference for well-architected data models, optimized query performance, and documented code.

You are proficient with at least one visualization & business intelligence platform (e.g., Sigma, Tableau, Looker, Mode).

Strong verbal and communication skills. You can articulate why something should be built a certain way and how it will impact the business.

You're comfortable working alongside AI tools and thinking critically about AI-generated output.

You expedite projects forward, favoring rapid and incremental development in parallel with problem-solving short-term obstacles.

You employ a structured approach to handle ambiguous exploratory analysis, balancing thoroughness with the MVP mindset.

You use excellent judgment and sharp business and product instincts that allow you to prioritize.

Experience working with a B2B software product.

Experience with dbt, Sigma, and Snowflake.

 Base salary for this role: $175k to $225k.

Tremendous is seeking a Senior Data Analyst to build reliable data models and semantic layers for AI-powered data access. This fully remote role involves partnering with Product, Finance, and Customer Success teams using SQL, dbt, Snowflake, and visualization tools like Tableau or Looker to drive data-informed decisions.

Senior Data Analyst

Global off-sites

Tremendous is the fast, free, flexible way to send bulk payouts to people in over 230 countries and regions. 20,000+ companies ranging from mom-and-pops to Google, MIT, and United Way have sent over $1 billion, saving 15 hours a month on average.

In both our product and our workplace, we’re intentional about making work more efficient, flexible, and fulfilling. Tremendous is a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life.

Our customers, who include marketers, researchers, HR teams, and nonprofits, rave about how quick and easy it is to use Tremendous — 

. Yet there’s a lot of complexity under the hood, including over 2,500 redemption options and plenty of banking infrastructure. This duality makes working here a fun challenge.

Tremendous is profitable and growing without outside investors. Join us before our next international offsite.

We are hiring an experienced data analyst to partner across our go-to-market teams (Sales, RevOps, Marketing, and Customer Success) and connect the full revenue funnel from acquisition through retention.

Tremendous values data as a first-class citizen and believes insights unlock significant growth. You will collaborate closely with the data team and company-wide stakeholders. As we continue to grow the business, you will scale GTM-focused insights and lead new data-driven initiatives.

Apply a range of analytics methods to gain insights across our go-to-market teams (sales, RevOps, marketing, and customer success), such as conversion funnels and attribution.

Identify and implement improvements within the Data team by standardizing processes, developing innovative practices, providing mentorship, and fostering new expertise.

Join a growing team of analysts and actively contribute to team collaboration and culture.

You have extensive experience with B2B GTM analytics across some or all of marketing, sales, RevOps, and customer success, and you are familiar with the related tools.

You are proficient with at least one visualization & business intelligence platform (e.g., Sigma, Tableau, Mode).

You use data to achieve ambitious goals and influence company-level outcomes. Experience as a technical lead or manager is a plus.

Experience with forecasting and predictive modeling.

Experience with operational tools and systems like Segment, Amplitude and Hubspot (or other CRM tools).

Communication

Tremendous is seeking a Senior Data Analyst, GTM to partner with sales, marketing, and customer success teams to connect the revenue funnel. You will utilize SQL and BI platforms like Tableau or Sigma to deliver actionable insights and drive data-informed decisions. This is a fully remote position available to residents across the Americas.

Senior Data Analyst, GTM

Build and own Tremendous’ partner-led growth motion, from early experimentation to repeatable programs.

Develop and deepen relationships with referral partners and Platform Clients that drive meaningful pipeline and revenue.

Establish clear positioning, enablement, and GTM alignment so partners know when, how, and why to bring Tremendous into deals.

Serve as the connective tissue between partners and internal teams, ensuring tight coordination across Sales, Marketing, Product, and RevOps.

Identify where structure, tooling, or process is missing and create it to help partners succeed at scale.

Use data and feedback from the field to prioritize opportunities, refine strategy, and guide investment in the partner ecosystem.

Experience building or scaling partnerships, programs, or revenue-adjacent initiatives in ambiguous environments.

Comfort owning outcomes, whether that’s pipeline or revenue.

Strong judgment and prioritization skills; you know what’s worth building now versus later.

Ability to work cross-functionally and move initiatives forward without formal authority.

A builder mindset: you enjoy starting with a blank page, testing ideas, and turning what works into playbooks.

Clear, thoughtful communication, especially in writing. We’re a documentation-first, low-meeting culture.

High ownership and autonomy. You take initiative, follow through, and don’t wait to be told what to do.

You’ll directly shape and scale Tremendous’ partnerships function.

Your impact on pipeline and revenue will be clear and measurable.

You’ll work cross-functionally with Sales, Marketing, Product, RevOps, and Data. This is a truly cross-functional role.

 Base salary for this role: $140,000 base salary ($200,000 OTE) and equity.

Tremendous is seeking a Partner Manager to build and scale its partner-led growth motion. The role involves developing relationships with referral partners, aligning GTM strategies, and coordinating across Sales, Marketing, and Product teams to drive pipeline and revenue. This is a fully remote position focused on creating repeatable partnership programs.

$190K – $220K • Offers Equity • OTE: $250k - 272k

Director of Partnerships

Partner Manager

 Package our business model and financials for external parties—whether that's potential partners, acquirers, or other stakeholders. Your investment banking background will be crucial here.

 Oversee and maintain detailed financial models that capture our complex revenue streams. Work with the Finance and Data teams to document assumptions, outputs, and scenarios in a way that's both rigorous and understandable.

 Help structure and price of complex enterprise deals. Work cross-functionally with sales, legal, and product to ensure deals are both financially sound and aligned with our strategic goals.

 Keep our financial forecasts updated, accurate, and defensible. Automate wherever possible.

 Dig into our data to identify trends, inefficiencies, and opportunities. Bring curiosity and analytical rigor to everything you do.

 As we grow, you'll have the opportunity to build out the finance team and establish best practices for financial operations.

 You've spent time in IB and know how to build complex financial models, tell a compelling financial story, and think about businesses from a strategic perspective.

4+ years at growth-stage startups (ideally at least one FinTech):

 You've led finance teams and owned the FP&A model at fast-moving startups and understand the pace and ambiguity that comes with it. You're comfortable making decisions with incomplete information.

 You’ve been intimately involved with multiple startup transactions, including at least one (either an investment or an acquisition) $100MM+

 You've worked on pricing and structuring complex enterprise deals, ideally in a B2B context.

 You genuinely enjoy building financial models and can get lost in Excel or other modeling tools. You care about getting the details right.

 You ask "why" and "what if" constantly. You're drawn to complex problems and enjoy digging into data to find answers.

 You've used Runway for FP&A and know how to leverage it effectively.

 You're excited to do the work yourself rather than delegating everything.

 We're profitable with no outside investors, which means no board meetings and no wasted time on investor relations. Your work will focus on actual financial planning and analysis.

 Our revenue model is sophisticated and multi-faceted. If you like easy, simple SaaS businesses, this isn't the role for you. If you like intellectual challenges, you'll love it here.

 Base salary for this role: $250,000 to $290,000.

Tremendous is seeking a Head of Finance to lead financial planning, analysis, and deal structuring. This fully remote role involves managing complex revenue streams, driving forecasting, and building out the company's finance function. The ideal candidate will leverage an investment banking background to support enterprise deals and optimize financial operations.

Head of Finance

We’re looking for a Founding European SDR to help launch and scale Tremendous’ outbound motion internationally. As one of our first international SDR hire, you’ll be responsible for identifying, engaging, and booking meetings with high-potential prospects, while helping define how we sell into new European markets.

You will partner closely with Account Executives to generate meetings and act as the first point of contact for prospective customers. This role requires strong outbound execution across email, phone, social, events, and field marketing, with meaningful ownership over account development and early market strategy.

As a founding hire, you will have the opportunity to shape messaging, process, and best practices for international sales while directly impacting pipeline, revenue growth, and Tremendous’ expansion internationally.

Work primarily to bring in new deals through outbound prospecting

Own your pipeline through cold calling first. The phone is your primary weapon; you'll be expected to make 100 cold calls per day, book meetings over the phone, and treat every unanswered call as the next opportunity to dial again. Email and LinkedIn support your outreach; they don't replace it

Collaborate with Account Executives, as well as members of our Marketing, Strategy, and RevOps teams, to develop new strategies to build our sales pipeline and grow our business

Use prospecting tools to research accounts, identify key contacts and craft targeted messaging

Learn our technology and effectively communicate our value proposition. Work to understand their goals and challenges to better understand how we can help.

You pick up the phone before you open email. Cold calling isn't something you tolerate - it's how you start your day, every day, without being told to.

Demonstrated history of consistently exceeding personal and professional goals, with a strong commitment to excellence in all endeavors

Curious, lifelong learner mindset with a passion for continuous improvement, staying updated on industry trends and best practices, and showing enthusiasm for applying newly acquired knowledge to improve job performance

Customer-obsessed sales approach, demonstrating a deep commitment to understanding and addressing the unique needs of our clients

Someone who is proficient in English and workplace proficient in at least one other language (preferably German, Spanish or French)

Independent. We all work together to solve tough problems here at Tremendous, but taking pride in experimenting and finding your own answers is the best way to learn.

Collaborative. When our SDRs uncover new trends and tactics that work to set meetings, they share them with their teammates so everyone can benefit.

Ambitious. Ambition isn't a dirty word at Tremendous. We're a team of achievers collaborating on a fast-growing product and that means personal growth in both role and responsibility as well as tons of personal upside for you.

 Base salary for this role: £37k - £45k. OTE: £52k - £60k.

Language Proficiency

Tremendous is seeking a Founding Sales Development Representative to launch and scale their outbound motion across Europe. This fully remote role involves high-volume cold calling, lead generation, and collaborating with Account Executives to drive international revenue growth. Candidates should be proficient in English and at least one other European language like German, Spanish, or French.

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