Location: This role is remote eligible in OH, KY, IN, IL, WI, or TN.
(Ideally within a 5-hour drive of CIncinnati, OH for occasional in-person meetings.)
Coaches and Consultants use Cloverleaf to coach more people, earn more revenue, and stay top of mind. Our insights reinforce coaching in-between sessions and scale a coach’s impact across teams. With Cloverleaf, clients keep growing, even when a coach isn’t in the room.
Our SaaS platform is based on deep psychology research and rooted in behavior science, with coaching tips unique to each individual’s strengths and powered by assessments like DISC, Enneagram, CliftonStrengths, and 16 Types.
Cloverleaf is on a mission to unleash people to do their best work. We believe that people should be passionate and engaged with the work that they are doing, starting with our own team.
The Role
Cloverleaf has garnered a remarkable track record in our few short years, and we’re primed and ready to take it to the next level. We’re looking for a Senior Account Executive with a
deep track record of selling into the coaching and consulting industry. This isn’t your typical SaaS sales job. It’s for someone who truly knows the coach and consultant audience - what they value, how they buy, and how to earn their trust.
It’s about relationships, not just pipelines.
You’ll join a high-performing team working a channel that has the support and backing of the entire organization, Cloverleaf leadership, and the Board of Directors.
The market is hungry - we’re getting more qualified leads than we can handle and we need the help of an experienced AE to convert those leads into lasting customer partnerships.
What You'll Do
Your job is
more than just closing deals. You’re helping the team build a new category of software that coaches and consultants are already asking for - automated, personalized coaching that reinforces their work and scales their impact.
- Own the full sales cycle for coaches and their clients, from prospecting to close
- Engage with qualified inbound leads (yes, there are a lot!) and build your own outbound pipeline
- Help coach partners understand how Cloverleaf adds value to their practice
- Team up with coaches to turn their clients into long-term Cloverleaf customers
- Provide feedback to shape our go-to-market messaging and product roadmap
- Collaborate with the Coach Channel Customer Success Manager to ensure long-term success
- Represent Cloverleaf at coaching industry events, trade shows, and conferences
- Keep CRM records clean, complete, and actionable
Who You Are
This role needs more than your “typical salesperson” - it needs a trusted advisor who
understands how coaches and consultants build their business. You understand the blend of passion, independence, and high standards they apply to their brand. You know how to anticipate their objections and speak their language. You know what it takes to win in the coaching and consulting world because you’ve done it.
You’ll love this role if you:
- Want to own and grow a high-potential channel in a fast-moving company
- Thrive on helping relationship-first buyers get better results for their clients
- See the power of assessments, insights, and scalable coaching technology
- Enjoy solving business problems more than pitching features
What You Bring
Required:
- 6+ years experience selling to independent coaches or consultants
- A consultative sales mindset: the ability to ask great questions, listen closely, and tailor solutions to the unique needs of each prospective customer
- Strong communication and relationship-building skills, especially with values-driven buyers
- Experience managing a full sales cycle in a remote-first team environment
- Familiarity using a CRM (i.e.: Salesforce) and managing pipeline metrics
Preferred:
- 10+ years total sales experience, ideally in SaaS or service-based environments
- Background in HR tech, talent development, or behavioral assessments
- Familiarity with tools like DISC, Enneagram, MBTI/16 Types, or StrengthsFinder
- Bachelor’s degree in a related field (business, psychology, communication)
How we help unleash you to do your best work
- Flexible PTO and work schedule - with a minimum of 2 full weeks off per year
- Company paid full benefits, including medical, dental, vision, life insurance, and more!
- Recognition rewards and monthly stipend for wellness, technology, pet care, or student loans
- Macbook and home-office set-up stipend
- 401k benefits including a 4% match with immediate vesting
- Truly values-driven team (ask us about it!)
Cloverleaf is committed to pay transparency and equitable compensation practices. The expected total compensation range for this role is $138,000-$170,000. This includes a base salary plus uncapped commission. Most new hires start toward the lower to middle end of this range, allowing for meaningful growth within the role as impact and performance increases over time. Final compensation is determined based on factors like experience and skills alignment.
