Enterprise Account Executive

About the company

The company is the leading provider of workplace financial wellbeing that blends fiduciary digital planning with access to one-on-one guidance from Certified Financial Planner™️ professionals. The company's award-winning program equips employees with a financial plan to guide them through decision points like budgeting, paying down debt, electing benefits, understanding equity compensation, starting a family, buying a home, saving for retirement, and more. Advanced reporting keeps our partners in the know, and drives results like reduction in financial stress, increased productivity, reduced employee turnover, greater use of pretax products, on-time retirement, and healthcare savings. The company members feel great about their money, allowing their work and wellbeing to thrive.

We’re a remote-first company, backed by prominent investors such as Ashton Kutcher’s fund Sound Ventures and Salesforce CEO Marc Benioff.

The Role

As the company’s Enterprise Account Executive , you will serve as a key driver of our growth by leading strategic sales efforts with Fortune 1,000 and multinational employers. This hands-on role owns the full enterprise sales cycle, from prospecting and discovery to presentation, proposal, and close. You’ll manage complex buying processes, build strong relationships with executive stakeholders, and position the company as the leading financial wellbeing solution in the market.

You will be a critical contributor to how we scale revenue in a high-growth, B2B2C, enterprise-focused environment. This role is ideal for a consultative sales professional who thrives in relationship building, strategic account management, and closing high-value opportunities.

This is a full-time, remote position which will require 25-30% travel.

Key Responsibilities

• Drive net new revenue by owning the end-to-end enterprise sales cycle, from prospecting and discovery through proposal, negotiation, and close.

• Build and manage a strategic pipeline of Fortune 1000 and multinational employer prospects, leveraging both outbound and inbound sources.

• Conduct consultative discovery to deeply understand prospect pain points and tailor the company solutions to meet their unique business, benefits, and workforce needs.

• Deliver compelling presentations, demos, and proposals to senior executives, including HR, Total Rewards, Benefits, and Procurement leaders.

• Collaborate cross-functionally with Marketing, Client Success, Product, and Operations teams to ensure alignment and maximize success.

• Navigate complex procurement and RFP processes, developing high-quality submissions with support from proposal and revenue operations teams.

• Build trusted relationships with benefits consultants, brokers, and channel partners to increase awareness and influence in the market.

• Consistently meet and exceed quarterly and annual revenue targets.

• Maintain accurate pipeline management and forecasting within CRM.

• Represent the company at industry conferences, webinars, and client-facing events.

Qualifications & Experience

• 5–7+ years of experience in enterprise SaaS sales or equivalent, ideally within employee benefits, Digital Health, HR tech, or fintech.

• Proven track record of meeting or exceeding annual quota.

• Strong knowledge of enterprise sales methodologies (e.g., MEDDIC, Challenger, SPIN).

• Experience running complex sales cycles with multiple stakeholders across HR, Finance, and Procurement.

• Excellent communication, storytelling, and presentation skills with C-level and senior HR/Benefits executives.

• Comfortable navigating RFPs and procurement processes.

• Collaborative, team-oriented approach with the ability to thrive in a fast-paced, high-growth environment.

• Familiarity with the benefits ecosystem and consultant/broker landscape is a plus.

• Passion for improving employee wellbeing and making a meaningful impact.

Benefits

• Remote-first company structure

• Medical, dental, and vision

• 401(k)

• Mental wellbeing (Talkspace)

• Financial wellbeing (the company)

• Paid vacation and sick leave

• Paid sabbatical after 5 years of service

• A supportive, inclusive team culture

• Opportunities for continuous learning and growth at a fast-growing startup at the cutting edge intersection of financial wellness and technology

Closing

The company strives to be an inclusive workplace and values learning from and engaging across different perspectives. Women, people of color, LGBTQIA+ individuals, and members of other minority or marginalized groups are strongly encouraged to apply.

The company is proud to be an equal opportunity employer and does not discriminate against candidates on the basis of race, ethnicity, color, national origin, age, religion, sex, gender, sexual orientation, gender identity, marital status, disability, or veteran status.

We are committed to fostering an environment that embraces diversity and inclusion and are seeking candidates from a variety of backgrounds, experiences, abilities, and perspectives to join our team. If you are interested in this opportunity but not sure if you fit this role, please apply and include a note to let us know of your interest. We’re excited to speak with you about joining our team!