The Opportunity  

We are looking for a Sr Account Executive to join our North American New Business team in selling Flywheel's service offerings to leading brands. This role focuses on our Supply Chain and Fee Recovery offerings – these services help brands identify operational inefficiencies, recover lost revenue, improve supply chain performance, and protect margin through disciplined recovery strategies and process optimization. 

As a Sr Account Executive, you will execute a consultative sales strategy within your assigned territory to drive revenue growth with target accounts. You will work in partnership with pre-sales and marketing teams to prospect and engage relevant stakeholders within target brands to develop opportunities across supply chain and fee recovery services. This role would be a great fit if you have sales experience, strong attention to detail and organizational skills, and exceptional communication skills to collaborate effectively with internal and external stakeholders. 

What You Will Do:  

• Contribute to revenue growth goals for your assigned territory by identifying and closing new business opportunities within Flywheel's Supply Chain and Fee Recovery offerings. 
• Develop a solid understanding of Flywheel's Supply Chain and Fee Recovery capabilities (e.g., fee recovery strategy, chargeback and claims support, vendor compliance opportunities, margin leakage identification, process optimization) and articulate how these solve client pain points. 
• Actively prospect and build a qualified new business pipeline through outreach and networking. 
• Manage mid-to-complex sales cycles from initial customer engagement through contract closure, with support from leadership as needed. 
• Support the creation of pitch decks and sales materials to effectively communicate Flywheel's capabilities and service offerings. 
• Maintain accurate lead, pipeline, and forecast reporting on a regular basis. 
• Collaborate with pre-sales and marketing on demand generation opportunities and use case development to engage prospective clients. 
• Work with the Client Services team to understand our value proposition and current market trends to position solutions effectively. 
• Attend networking events to build relationships and identify potential clients. 
• Stay informed on industry news and translate relevant trends in supply chain operations and cost recovery into client conversations. 

 Who You Are:  

• You have 5+ years of sales experience, selling solutions to mid-market and enterprise companies (experience selling supply chain, operations, logistics, analytics, or related services is a plus). 
• You have experience building and maintaining external relationships to achieve mutual business goals; you are comfortable engaging stakeholders at various organizational levels. 
• You have a solid understanding of the sales process and proven ability to move opportunities through the pipeline. 
• You are motivated, have a strong work ethic, and thrive in a fast-paced environment. 
• You are a strong communicator, naturally curious, and genuinely care about client outcomes. 
• You have a solutions-oriented mindset and can navigate ambiguity to identify client needs and appropriate solutions. 

This role is commission eligible. 

#LD-AD1

Human Interest is on a mission to ensure that people in all lines of work have access to retirement benefits. 

More than half of all working Americans are not saving enough for their future. Too often, it’s because they are employed by a company that doesn’t offer a retirement plan. Human Interest is changing that by making it affordable and accessible for small and medium-sized businesses to offer employees a path to financial independence through retirement savings.

We’re a high-growth fintech company changing the retirement industry. We are backed by a number of investors. This includes funding from Marshall Wace and Baillie Gifford, as well as top investors such as BlackRock, TPG (The Rise Fund), SoftBank, Glynn Capital, NewView Capital, USVP, Wing, Uncork, and more.

About the role

Our Partnership Program is a key initiative for the company. The Partner Account Manager’s primary duty is to engage, build and develop Human Interest’s key accounts and growth opportunities. We're looking for a forward-thinking, meticulously organized, and self-motivated sales professional who can thrive in a fast-paced environment.  You'll accelerate our partner relationships to help us exponentially reach more small and medium businesses across the United States, which is essential to our growth. This role requires someone who is proactive, creative, and can exercise their own discretion and judgment to create their own solutions when needed.

What you get to do every day

• Develop, build, and amplify referral relationships with tech partners, human capital management partners, benefit brokers, CPA's and financial advisors in the SMB space
• Create and build strategic referral networks and partnerships focused on lead generation and new partnership opportunities 
• Proactively identify and resolve emerging issues and offer solutions by working cross-functionally with Sales, Product, Marketing, Legal and Finance 
• Collaborate with Partner Marketing to innovate and execute unique initiatives to promote partner sales (e.g, educational events, email, webinars, etc.)
• Work with partners to establish business goals and performance metrics (e.g, depth of sales pipeline and revenue generation) to develop and execute effective go-to-market strategies and demand-generation activities

What you bring to the role

• 2+ years of experience building, developing, and maintaining relationships with tech and human capital management (HCM) partners, benefit brokers, CPA's and financial advisors in the SMB space (including territory sales and business development)
• Successful - Proven track record of success in a quota driven sales environment
• Passionate - You are a highly motivated individual contributor and relationship builder that can operate independently
• Dynamic - You can thrive in a fast-paced, and ever-changing environment
• Resilient—You bounce back from setbacks quickly, are resourceful, and find creative ways to get things done.
• Solutions-oriented - Willingness to get your hands dirty while managing and solving operational partnership issues
• Extraordinary communication and interpersonal skills — people trust you and sense that you are advocating for something you believe.
• Tech-savvy - familiarity using Salesforce to manage sales cycles is preferred
• Growth mindset - You can embrace feedback and hold yourself accountable.
• Coachable- Ability to absorb information, training, and guidance and successfully implement and execute
• Travel - Ability to be In the field 3 days/week

Why you will love working at Human Interest

Human Interest is tackling one of our country's biggest challenges - closing the retirement gap. You'll be instrumental in architecting and scaling solutions that bring financial security to employees at small and medium-sized businesses nationwide. We’ve made significant progress, but there is still growth ahead, offering you a unique opportunity to solve complex problems, drive innovation, and advance your career alongside a dedicated, mission-driven team. We value hard work and recognize that our team's contributions are key to our continued success.

Join Human Interest and make a lasting impact by shaping the future of retirement.

Our operating principles define how we work together as a team. They reflect Human Interest’s unique view on what’s important and what’s right. Documenting this core aspect of our culture helps employees make good decisions on their own. It also helps candidates considering career opportunities critically evaluate whether they will thrive at Human Interest. 

• Customer obsession: We're all about creating amazing experiences for our customers. We put their needs first and go the extra mile to make them smile.
• Long-Term Orientation: We're not just playing for today; we're building a legacy. We think big, plan strategically, and invest in our future.
• Autonomous and Accountable Teams: We trust our team members to take ownership and make smart decisions. We empower you to be your best self!
• An Escalating Bar for Talent and Performance: We're constantly raising the bar and challenging ourselves to be better. We believe in growth and continuous improvement.
• Fundamental Optimism: We see the glass as half full (and then we fill it up with more amazing ideas!). We believe in the power of positivity and the potential for greatness.

Compensation - At Human Interest, we consider a number of factors to determine the appropriate pay range for each position, including the cost of labor in different markets across the U.S. The total On Target Earnings (OTE) for the role described in this job posting is $135,000 - $140,000 which includes a base salary of $70,000, and a variable target compensation of $70,000. The specific pay rate offered is based on the candidate’s relevant skills and experience. Base pay is just one component of our Total Rewards package, which also includes a comprehensive suite of physical, financial, and mental wellness benefits. Additionally, employees receive stock option grants, enhancing long-term financial growth and investment in our company's success.

Benefits - 

• A great 401(k) plan: Our own! Our 401(k) includes a dollar-for-dollar employer match up to 4% of compensation (immediately vested) and $0 plan fees
• Top-of-the-line health plans, as well as dental and vision insurance
• Competitive time off and parental leave
• Addition Wealth:  Unlimited access to digital tools, financial professionals, and a knowledge center to help you understand your equity and support your financial wellness
• Lyra: Enhanced Mental Health Support for Employees and dependents  
• Carrot: Fertility healthcare and family forming benefits
• Candidly:  Student loan resource to help you and your family plan, borrow, and repay student debt
• Monthly work-from-home stipend; quarterly lifestyle stipend
• Engaging team-building experiences, ranging from virtual social events to team offsites, promoting collaboration and camaraderie.

We’re a great place to work (but don’t take our word for it) 

Here’s a list of our awards and accolades:

• Certified as a Great Place To Work® (2023-2025)
• Fortune Best Place to Work in the Bay Area (2024)
• Best Places to Work by Built In (2023-2024)
• America’s Best Startup Employers by Forbes (2020-2022, 2024) 
• A Top Company by Y Combinator (2020-2023)
• Inc. Fastest Growing Companies (2021)

Human Interest is an equal opportunity employer. All applicants will receive consideration for employment without regard to race, color, religion, sex, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran or military status, pregnancy, or any other characteristics protected under federal, state, or local laws.

We are committed to making every stage of our application process fully accessible to all individuals. If you need a reasonable accommodation at any point in the process, please let us know at applicantaccommodations@humaninterest.com.

Protect yourself against fraud and identity theft. Apply to our open positions directly via our careers page on Greenhouse. Human Interest will never ask applicants for their financial or banking information as part of our application process. All legitimate communication will come from a @humaninterest.com email address. If you have questions, please reach out to us directly at careers@humaninterest.com

Please note Human Interest does not accept unsolicited resumes from any source other than directly from candidates. We will not consider resumes from vendors, including and without limitation search firms, staffing agencies, fee-based referral services, and recruiting agencies. 

Pursuant to the San Francisco Fair Chance Ordinance, we will consider employment-qualified applicants with arrest and conviction records. We comply with CCPA guidelines.

See more: https://humaninterest.com/disclosures

The Opportunity  

We are looking for a Senior Director, Omni Channel Sales (Walmart/Target) to join our North American New Business team and drive strategic revenue growth across some of the world’s largest brands. This role will focus specifically on accelerating Flywheel’s growth within the Walmart and Target segments, building senior-level relationships, identifying high-value opportunities, and expanding our presence across priority accounts.

As a Senior Director, you will develop and lead a consultative sales strategy within an assigned portfolio of target brands, with a focus on unlocking enterprise-level partnerships and long-term commercial success. You will work cross-functionally with pre-sales, marketing, product marketing, and client services teams to shape compelling solutions, engage executive stakeholders, and drive opportunities through the full sales lifecycle.  

This role is ideal for a highly strategic, commercially minded sales leader with deep experience selling into large brands, ideally across retail media, commerce, CPG, or adjacent digital services. You bring executive presence, strong business acumen, and a proven ability to influence complex buying groups while translating market trends into meaningful client solutions. 

What You Will Do:  

• Own and drive revenue growth against goal for a defined portfolio of targeted brands within the Walmart and Target segments  
• Develop and execute a strategic new business plan to grow Flywheel’s presence with large enterprise brands and priority prospects  
• Build, manage, and advance a qualified pipeline of new business opportunities, with a focus on high-value, multi-service engagements  
• Lead complex, consultative sales cycles from initial engagement through solution development, negotiation, and close  
• Build and maintain senior and executive-level client relationships, serving as a trusted advisor to key decision-makers across prospective accounts  
• Act as a subject matter expert on Flywheel’s capabilities, services, and value proposition, clearly articulating how our solutions solve client pain points and drive measurable outcomes  
• Partner with internal stakeholders to shape and deliver tailored proposals, business cases, and pitch presentations that align Flywheel’s offerings to client priorities  
• Translate industry news, macro trends, retailer dynamics, and competitive developments into actionable recommendations for prospects and clients  
• Collaborate closely with pre-sales, product marketing, and marketing teams to create joint demand generation strategies, use cases, and account-based engagement plans  
• Work with Client Services and broader commercial teams to ensure strong alignment on service capabilities, go-to-market messaging, and market demand  
• Maintain accurate and disciplined lead, pipeline, and forecast reporting, providing visibility into performance, opportunity health, and revenue outlook  
• Represent Flywheel at industry events, trade shows, and networking opportunities to build market presence and identify future clients  
• Contribute to the ongoing refinement of sales strategy, territory planning, and commercial best practices across the broader North American New Business team  
• Mentor and influence others across the organization through leadership, collaboration, and a strong point of view on market opportunities and growth strategy 

Who You Are:  

• You have 10+ years of sales or business development experience, with a strong track record of selling mid-market to enterprise solutions into large organizations 
• You have meaningful experience working within or selling into Walmart and/or Target ecosystems; experience in retail media, commerce, CPG, or digital marketing services is strongly preferred 
• You have a proven ability to build executive relationships, navigate complex organizations, and align multiple stakeholders around a strategic solution 
• You bring a strong understanding of the end-to-end enterprise sales process, including prospecting, solution development, negotiation, forecasting, and closing 
• You are a highly motivated hunter with the strategic mindset to identify, develop, and convert large-scale business opportunities 
• You are an exceptional communicator who can confidently engage audiences from day-to-day operators to senior executives 
• You are naturally curious, commercially sharp, and deeply focused on delivering positive client outcomes 
• You have a solutions-oriented mindset and are comfortable operating in ambiguity, solving complex problems, and building structure where needed 
• You can analyze performance dashboards and use spreadsheets, including Excel formulas and pivot tables, to extract insights and tell a clear story from imperfect or complex data 
• You are highly organized, detail-oriented, and able to manage multiple priorities and sales opportunities simultaneously 
• You have a strong sense of ownership and a bias for action, with a willingness to roll up your sleeves and do what it takes to move the business forward 
• You are a collaborative team player who contributes positively to cross-functional partnerships and the overall success of the team 
• You are comfortable traveling as needed 

This position is commission eligible. 

The Opportunity  

We are looking for a Business Development Director to join our North American New Business team in selling Flywheel’s service offerings to some of the world’s largest brands. This role focuses particularly on our Content Operations – this service produces content & creatives that help elevate brand visibility and drive conversions.  

As a Business Development Director, you will develop and execute a consultative sales strategy within an assigned territory to drive revenue growth with leading brands. You will work in partnership with the pre-sales and marketing teams to prospect and engage relevant stakeholders within targeted brands to develop opportunities across all relevant services and markets, managing these throughout the sales process until completion. This role would be a great fit if you have previous experience in sales, a high attention to detail and organizational skills, and exceptional communication skills to collaborate effectively with internal and external stakeholders across all levels. 

What You Will Do: 

• Be responsible for revenue growth to goal for a specific territory of targeted brands for Flywheel’s Content Operations offerings. 
• Act as a subject matter expert in Flywheel’s Content Operations capabilities (e.g., product copy, rich media, imagery, content health and compliance, content syndication, localization) and how these solve client pain points and drive measurable business outcomes. 
• Actively prospect and develop a qualified new business pipeline 
• Manage complex sales-cycles from initial customer engagement to closed sales  
• Participate in end-to-end business planning; you will build comprehensive pitch decks and defend through proof points to effectively communicate Flywheel’s capabilities and service offerings in support of client needs 
• Manage accurate lead, pipeline, and forecast reporting on a regular basis  
• Collaborate with pre-sales and product marketing to create join demand generation strategies and potential use cases to engage prospective clients  
• Collaborate with the Client Services team to ensure we have command of the value proposition for all products and services, as well as current trends, and market demands. Possess the ability to communicate to prospective Clients how we can help their business challenges and promote growth 
• Attend networking events to promote Flywheel solutions and identify potential future clients 
• Have a pulse and opinion on industry news, translate macro trends into tailored recommendations and actions for clients  

Who You Are: 

• You have 7+ years of sales experience, selling mid-market to enterprise solutions into large companies (experience selling retail media/CPG would be an asset) 
• You have experience managing external relationships to meet mutually beneficial goals; speaking with executives of different levels of an organization comes naturally to you 
• You have a comprehensive understanding of the end to ends sales process 
• You thrive in a fast-paced environment and have a highly motivated hunter mentality 
• You are a strong communicator, naturally curious, and genuinely care about client outcomes 
• You have a solutions-oriented mindset and thrive in ambiguity and figuring out solutions and processes to complex problems 
• You feel comfortable analyzing dashboards and utilising spreadsheets using Microsoft Excel formulas and pivot tables to extract and clearly communicate insights from murky data 
• You have a bias for action with a scrappy willingness to roll up your sleeves and go the extra mile to persist and get the job done 
• You have a sense of ownership complemented by strong organization skills and a keen eye for detail 
• You can effectively lead and manage project the ability to efficiently prioritise and execute projects 
• You are a team player with a genuine desire to contribute to the overall success of the entire team 
• You are able to travel as needed 

This position is commission eligible.