VP, Small Business Sales

The Opportunity 🚀

As VP, Small Business Sales, you will own and scale Carrot’s SMB revenue engine.

This is not a maintenance role. It is a build-and-scale leadership opportunity with meaningful visibility across the business. You will shape the strategy, structure, operating rhythm, and execution model for one of Carrot’s most important growth segments.

You will lead a team of SMB sales representatives and work closely with Marketing, Revenue Operations, Product, Customer Success, Finance, and other Sales leaders to sharpen our go-to-market approach, strengthen our broker and consultant ecosystem, improve conversion, and create a repeatable path to revenue growth.

You will also be a key voice in executive-level customer conversations, helping position Carrot with HR, Benefits, Finance, and C-suite stakeholders who are making important decisions about how to support their people.

The right leader will bring strong commercial judgment, a builder’s mindset, operational discipline, and the ability to inspire teams to do ambitious, meaningful work.

What You’ll Own 💼

In this role, you will:

• Develop and execute the SMB sales strategy to consistently achieve or exceed revenue goals.
• Lead, coach, and scale a team of approximately 8–10 SMB sales representatives.
• Build a high-performance culture rooted in clarity, accountability, strong coaching, and continuous improvement.
• Design and operationalize the SMB sales engine, including forecasting, pipeline management, deal strategy, performance inspection, and sales cadence.
• Establish clear KPIs, operating rhythms, and leading indicators that drive consistent execution.
• Engage directly in strategic customer conversations with HR, Benefits, Finance, and executive stakeholders.
• Lead or support complex, multi-threaded deals when executive presence or strategic support is needed.
• Strengthen relationships with brokers, consultants, and channel partners who influence employer buying decisions.
• Own forecasting accuracy, pipeline visibility, and business performance for the SMB segment.
• Partner cross-functionally to improve messaging, pricing, packaging, enablement, and go-to-market effectiveness.
• Bring structured market feedback into Product and Marketing to influence roadmap, positioning, and buyer engagement.
• Help define what excellent SMB sales execution looks like at Carrot as the business continues to scale.

What Success Looks Like 📈

In your first 12–18 months, you will have:

• Built a predictable, scalable SMB sales engine with clear operating discipline.
• Established a repeatable path to SMB revenue growth.
• Improved team performance through stronger coaching, clearer expectations, and better execution.
• Strengthened Carrot’s presence with SMB buyers, brokers, consultants, and benefit influencers.
• Increased forecasting discipline, pipeline visibility, and leadership confidence in segment performance.
• Identified opportunities to improve packaging, positioning, and sales effectiveness.
• Helped define how Carrot wins in SMB for years to come.

About You ✨

You are a sales leader who knows how to build. You bring the discipline to run a strong business, the creativity to shape a growing market, and the leadership presence to inspire a team through scale.

You likely have:

• 8–10+ years of sales experience, including meaningful sales leadership experience.
• A track record of leading, coaching, and developing high-performing sales teams.
• Experience owning measurable revenue targets and driving consistent performance.
• Success selling complex, multi-stakeholder solutions to HR, Benefits, People, Finance, Healthcare, or executive buyers.
• Strong executive presence and confidence engaging senior decision-makers.
• Experience building or scaling a sales motion, not only managing an established one.
• Strong forecasting discipline and a data-driven approach to pipeline, performance, and team management.
• Comfort operating in a fast-moving, high-growth environment where strategy and execution happen in parallel.
• Experience working with brokers, consultants, channel partners, or other influencers in the sales process.

Nice to Have ⭐

While not required, we would be especially excited if you bring:

• Experience selling employer-sponsored healthcare, benefits, fertility, family-forming, hormonal health, or digital health solutions.
• Experience scaling or transforming a sales segment in a high-growth company.
• Familiarity with fully insured and self-funded employer benefit models.
• Experience building repeatable sales motions in SMB, mid-market, or benefits-driven markets.

Why This Role Matters 🧡

This role sits at the intersection of mission, market opportunity, and business growth.

The SMB segment represents a meaningful opportunity to expand access to Carrot for more employers and more employees. Many smaller organizations want to offer best-in-class benefits but need a partner who can make the buying process clear, scalable, and actionable.

As VP, Small Business Sales, you will help build that path.

You will have the opportunity to shape a growth engine from the ground up, influence how Carrot shows up in the market, develop a high-performing team, and create lasting impact for employers and families.

Interview Process 🤝

We take hiring seriously and believe a structured, transparent process helps both sides make the right decision.

For this role, you can expect:

1. Intro Call with Recruiting — 30 minutes
2. 3 -Minute Video Pitch 
3. Sales Leadership & HRBP Panel — 45 minutes
4. Cross-functional Panel — 45 minutes
5. Hiring Manager Interview — 45 minutes

Throughout the process, we will share context on the team, business strategy, expectations, and what success looks like. We encourage candidates to use each step to evaluate whether Carrot and this role are the right fit for their career, leadership style, and goals.

Why Candidates Join Carrot 🌍

Carrot offers the opportunity to do commercially meaningful work in service of a deeply human mission.

Our leaders are empowered to build and shape how we scale. We value ownership, thoughtful execution, collaboration, and long-term thinking.

Highlights include:

• A high-trust, high-ownership culture where leaders are empowered to build and scale.
• A mission-driven business with meaningful market demand and real-world impact.
• Competitive equity with a long-term focus on value creation.
• Flexible Time-Off. Actively promote healthy time off habits to ensure people are actually disconnecting and recharging.
• Comprehensive parental leave and family-forming support for employees and their families.
• A modern, flexible work environment designed to support productivity, collaboration, and balance.
• The opportunity to help expand access to care for people navigating fertility, family-forming, and hormonal health journeys.

Compensation 💰

Carrot offers a holistic Total Rewards package designed to support employees in all aspects of life inside and outside of work. This includes health and wellness benefits, retirement savings plans, short- and long-term incentives, parental leave, family-forming assistance, and more.

The starting base salary for this role is $185,000–$200,000, with actual compensation varying based on experience, skills, and job-related factors. Certain roles are eligible New Hire Stipend, Coworking Stipends and Productivity Stipends.

Fraud and Security Notice 🔒

All communication regarding job opportunities at Carrot will come exclusively from an @get-carrot.com email address. If you receive messages from any other domain, please disregard them and report the incident to securityreporting@get-carrot.com.

Client-provided location(s): Flexible / Remote

Job ID: 5986616004

Employment Type: OTHER

Posted: 2026-05-04T23:29:14