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.

Carrot is seeking a strategic and people-focused Manager, Business Intelligence to lead and scale our growing BI function. This role will oversee a team of Business Intelligence Analysts while advancing our reporting, analytics, and data infrastructure capabilities across the organization.

You will play a critical role in enabling data-informed decision-making by partnering closely with leaders across Finance, Product, Engineering, Customer Success, Sales, and Business Development. The ideal candidate brings strong technical expertise, proven people leadership experience, and the ability to translate complex data into actionable insights.

This role reports to the VP, Data & Business Intelligence.

What You’ll Do

Lead & Develop the BI Team

• Manage, mentor, and grow a team of Business Intelligence Analysts and Data Engineers
• Establish clear goals, development plans, and performance expectations
• Build a culture grounded in accountability, quality, and impact

Drive BI Strategy & Execution

• Partner with leadership to shape and execute Carrot’s BI roadmap
• Translate business priorities into scalable analytics solutions and reporting frameworks
• Implement structured processes for intake, prioritization, and delivery of BI initiatives
• Ensure alignment between data initiatives and company-level KPIs

Strengthen Data Infrastructure & Governance

• Oversee data modeling standards and analytics best practices
• Evaluate and recommend tools and vendors to enhance our data stack
• Champion data governance, documentation, and quality assurance
• Ensure reliable, timely, and actionable reporting for stakeholders

Collaborate Cross-Functionally

• Lead requirements gathering with business teams
• Bridge technical and non-technical stakeholders
• Communicate insights clearly to diverse audiences
• Drive adoption of BI tools and self-service analytics

What You’ll Bring

• 5–8 years of experience building or scaling business intelligence or analytics functions
• 1–3+ years of people management experience, including coaching and performance management
• Experience in high-growth environments; experience in regulated industries (e.g., healthcare, finance, insurance) is a plus
• Strong knowledge of data modeling and analytics systems architecture
• Advanced SQL skills (joins, CTEs, window functions)
• Working knowledge of statistics, experimentation, and measurement frameworks
• Experience with BI tools such as PowerBI, Tableau, Looker, or DOMO
• Ability to translate business needs into technical execution and executive-ready reporting
• Strong communication skills and stakeholder management experience

Nice to Have

• Familiarity with healthcare data
• Working knowledge of Python

Compensation: 

Carrot offers a holistic Total Rewards package designed to support our employees in all aspects of their lives inside and outside of work, including health and wellness benefits, retirement savings plans, short- and long-term incentives, parental leave, family-forming assistance, and a competitive compensation package. The starting base salary for this position will range from $150,00000 - $175,000.00. Actual compensation may vary from the posted base salary depending on your confirmed job-related skills and experience. 

Fraud and Security Notice: Please note that 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

Carrot is seeking a Demand Generation Manager, Consultants & Employers, who will own pipeline creation with consultants/consulting houses and domestic and global employer, public sector, and union audiences, working hand‑in‑hand with Consultant Relations and segment sales teams. You’ll build campaigns that educate and activate consultants as advocates, and convert their employer clients into qualified opportunities for Carrot.

This role is part of the Demand Generation team and is central to our consultant and employer workstreams in the Demand Creation initiative.

Responsibilities:

Drive demand through consultants and consulting houses

• Build and execute a consultant demand strategy and program calendar, aligned with Consultant Relations and segment leadership.
• Design and run consultant-facing campaigns (e.g., briefings, webinars, events, newsletters, toolkits, playbooks) that keep Carrot top‑of‑mind and make it easy for consultants to recommend Carrot to their clients.
• Partner with Consultant Relations to segment and prioritize firms and key influencers, and to ensure outreach and follow-up align with relationship strategies.

Run integrated campaigns to reach employers

• Create campaigns for employer prospects influenced by consultants and partners, including large enterprise, global and union employers, through webinars, events, email nurtures, and targeted outreach.
• Collaborate with Product Marketing to tailor messaging and content by segment and buyer persona.
• Enable Sales and SDRs with campaign briefs, sequences, and follow-up guidance that connect consultant touchpoints to employer opportunities.

Execute, measure, and optimize programs

• Partner with Marketing Operations and the Digital team to launch campaigns across email, Outreach, web, and events, ensuring clean targeting and tracking.
• Set clear goals for each program and test tactics to improve conversion at each stage of the funnel.
• Define and own targets for consultant‑sourced pipeline, consultant‑influenced pipeline, marketing‑sourced employer pipeline, and won revenue across priority segments (U.S., global, unions), and use those insights to refine where we invest.

Codify repeatable consultant & employer “demand patterns”

• Turn successful consultant and employer motions into standardized plays that can be reused across regions and segments.
• Document workflows, audiences, and assets so these programs can be scaled, reported on, and supported by additional DG headcount over time.
• Contribute to the broader Demand Creation system, ensuring consultant and employer motions are connected with direct, partner, and global plays.

The Team: 

This role sits on our Demand Generation team, reporting to the Director of Demand Generation, within the larger Marketing department. You will partner most closely with the Consultant Relations, segment sales teams, Product Marketing, and RevOps.

Minimum Qualifications: 

• A Bachelor’s Degree
• 4–6 years of B2B demand generation, field marketing, or ABM experience targeting large employers and intermediaries, like consultants, brokers, and advisors.
• Background in healthcare, employee benefits, or HR technology marketing.
• Proven success designing and executing multi-touch campaigns that drive meetings and pipeline.
• Experience partnering with Sales and relationship‑owning teams, like Consultant Relations and Partnerships, on shared targets and plans.
• Experience with account-based or segment-based strategies, including working from target account lists and segment plans.
• Comfort working in a fast‑changing environment and helping to build new systems from the ground up.

Preferred Qualifications:

• Experience marketing through or to benefits consultants, brokers, or consulting firms.
• Familiarity with Marketo (or similar MAP), Salesforce, Outreach, and webinar platforms (e.g., Zoom/Wistia).
• Experience with account-based or segment-based strategies, including working from target account lists and segment plans.
• Comfort working in a fast‑changing environment and helping to build new systems from the ground up.

Compensation: 

Carrot offers a holistic Total Rewards package designed to support our employees in all aspects of their life inside and outside of work, including health and wellness benefits, retirement savings plans, short- and long-term incentives, parental leave, family-forming assistance, and a competitive compensation package. The starting base salary for this position will range from $96,000-$130,000. Actual compensation may vary from posted base salary depending on your confirmed job-related skills and experience. 

Fraud and Security Notice: Please note that 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

The Role

Interested in Carrot, but don’t see an open position that aligns with your background? Let’s Connect.   

While we may not have an open position now that aligns with your background, we are always looking for good talent and may have future opportunities suited for your skillset and expertise. By connecting with us, we will have access to your resume and application information for future reference, and we will be sure to reach out if something aligns, and to keep you informed about new positions. As always, if you see any opportunities that open up, please also feel free to submit your application to those roles as well!

We love that you want to help us in our mission of making fertility care accessible to all, and we hope to chat with you soon!