Full-Time

Director – GTM Strategy

Posted on 10/31/2025

Tremendous

Tremendous

51-200 employees

Global B2B rewards distribution platform

Compensation Overview

$180k - $220k/yr

+ Base Salary

Remote in USA

Remote

Category
Business & Strategy (2)
,
Requirements
  • 4+ years of experience in some combination of: Highly strategic work such as investment banking or consulting
  • Being an operator at a start-up
  • Startup experience owning 0-to-1 projects with hands-on execution, not just stakeholder management
  • Strong written communication skills. We’re a documentation-first culture.
  • Desire and ability to work autonomously and drive your work. Tremendous is not a great fit for people who default to waiting for instructions.
  • A highly motivated self-starter who is eager to make an impact and unafraid of tackling large, complex problems while delivering high-quality results.
  • Someone who enjoys collaborating with sales, marketing, and product managers.
  • Comfortable taking on the role of a Project Manager to drive results.
  • Able to prioritize and re-visit priorities accordingly.
Responsibilities
  • Identify and synthesize the strategic opportunities for the company. You will lead the scoping and research of our longer term GTM priorities. You will also own sharing out recommendations and updates with company leadership.
  • Translate insights into action. We’re a small and fast-moving enough start-up that you will need to roll your sleeves up and drive implementation. You will be reporting to our VP of Revenue, and you will own meaningful projects through implementation. For example, you wouldn’t just come up with an idea for a new business line but you’d test the idea, iterate, talk to potential customers yourself (with support from other folks as needed).
  • Collaborate cross-functionally to get the job done. Own strategic initiatives and be the one accountable to get them over the line. You will be one of the most cross-functional players at the organization and will work across sales, marketing, product, and data.

Tremendous provides a B2B platform for sending payouts and rewards globally. It offers a catalog of over 2,000 reward options, including gift cards and digital payments, which allow recipients to choose rewards that are valuable to them. Clients manage distributions via bulk uploads or individual transactions, and Tremendous handles end-to-end delivery, with instant fulfillment and easy redemption. The platform integrates with more than 5,000 tools, enabling seamless incorporation into existing systems. Unlike many competitors, Tremendous has grown profitability without venture capital and began as a Y Combinator-backed startup, highlighting a history of sustainable growth. Its goal is to help organizations run efficient, scalable incentive programs and payout workflows worldwide by providing flexible rewards and reliable delivery.

Company Size

51-200

Company Stage

Early VC

Total Funding

$630K

Headquarters

San Francisco, California

Founded

2010

Simplify Jobs

Simplify's Take

What believers are saying

  • Crossed $1B payouts, serving Google, Stripe, Atlassian with 10,000+ clients.
  • G2 Best Software Award for fastest growth in rewards category.
  • Hired Craig Whitmer as VP Sales with 25+ years experience.

What critics are saying

  • Stripe and Google internalize payouts, cutting Tremendous dependency in 12-24 months.
  • ADP and Workday expand into incentives, eroding core use cases in 18-36 months.
  • California AB 2863 mandates escrow, destroying low-margin economics in 12-18 months.

What makes Tremendous unique

  • Tremendous offers 2,000+ redemption options including Visa and Amazon gift cards.
  • Integrates with 5,000+ tools for seamless automated global payouts.
  • Free platform charging only sent amounts, fully self-funded since 2011.

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Benefits

Remote work

Apple equipment

Unlimited vacation

Learning budget

Parental leave

Health, dental, & vision

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

0%

2 year growth

1%
Yahoo Finance
Nov 8th, 2023
Tremendous Appoints Former Asana and Google Exec as Vice President of Marketing as Platform Crosses $1 Billion in Payout Transactions

In addition to its Vice President of Marketing appointment, Tremendous recently promoted Angie Peng to Vice President of Strategy and Sales.

FF News
Aug 17th, 2022
Tremendous Names Craig Whitmer Vice President Of Sales

Tremendous, a payouts platform enabling businesses to send money to anyone around the world, named Craig Whitmer as Vice President of Sales. “The Tremendous team built a platform that’s already been adopted by some of the world’s premier institutions — and they did it with a small but mighty team,” Whitmer said. “That’s a testament to the quality of their people and their product. I’m so excited to help Tremendous achieve its next stage of growth.”

Digi Influence
Aug 17th, 2022
Awe-inspiring Names Vice-president of Sales, Craig Whitmer

Tremendous, a payouts platform enabling businesses to send money to anyone around the world, named Craig Whitmer as Vice President of Sales.

INACTIVE