Director of Sales

About the Role

Chicory is growing, and we're looking for a Director of Sales who is energized by building high-performing teams and translating big-picture revenue strategy into day-to-day execution. This is a pure people leadership role where your success is measured by the success of your team. Sitting between our CRO and a team of sellers, you'll be the connective layer that turns vision into results. This role is for a seasoned sales leader who knows how to develop sellers at varying levels; you'll coach deals, raise the floor of your team, and create an environment where our team is motivated to do their best work.

Responsibilities

• Own team quota attainment end-to-end, actively managing pipeline health, forecast accuracy, and the interventions needed to keep the team on track each quarter, including performance management
• Coach and develop a team of sellers through 1:1s, deal reviews, and call coaching, with a focus on scaling growth
• Translate the CRO's revenue strategy into a clear, executable team plan, including territory design, account prioritization, and outreach frameworks
• Deliver accurate, data-informed forecasts to the CRO on a weekly and quarterly basis, proactively identifying pipeline risk
• Build and maintain a documented, repeatable sales playbook
• Partner cross-functionally with Marketing, Client Success, Campaign Management, Product, and Partnerships to remove blockers and deliver seamless client experiences
• Attract, onboard, and retain high-performing sellers, addressing underperformance early and creating clear growth paths for top talent
• Externally facing with customers, regularly joining sales calls, building leveled-up client relationships, and meeting with customers in the field
• Serve as the primary escalation point for complex deals, renewals, and client relationships that require senior involvement
• Keep the CRO informed with honest, well-synthesized reporting and execute on decisions with speed and clarity
• Build upon team and company culture and act as a champion of the Chicory Principles

Qualifications

• 7+ years of sales experience, with 4+ years in a people management role leading a team of quota-carrying sellers
• Proven track record of hitting or exceeding team revenue targets in a digital media, shopper marketing, and CPG environment
• Experience building or significantly improving a sales process, including pipeline management, forecasting methodology, and coaching frameworks
• Strong ability to develop sellers at varying skill levels, from onboarding new hires to elevating tenured sellers
• Data-driven mindset with the ability to diagnose team performance gaps and act on them quickly
• Excellent communicator who can synthesize complex information for a CRO and translate strategy clearly for a seller
• Comfortable operating in a fast-moving, dynamic environment where priorities shift and ambiguity is the norm
• Ability to travel 20% of the time to engage with clients and attend events

The base salary range for this position is $175,000 - $185,000 annually.
Location: Remote or New York/Hybrid

Benefits & Perks

Focusing on your health and wellbeing:

• Comprehensive healthcare benefits, including dental + vision plans
• Flexible paid time off policy for vacation, sick days, mental health days, and more!
• 14 paid holidays + flexibility to take paid time off for any other holidays you observe
• Employer-paid membership to One Medical
• Free ClassPass membership

Creating a culture in which you can thrive:

• Annual learning & development stipend
• Flexible remote and hybrid work style arrangements
• Fun and friendly office in NYC stocked with free snacks
• Virtual and in-person outings and fun activities with our amazing team 
• Dog-friendly workplace

Supporting you financially:

• Competitive compensation package, including base salary + stock options
• Flexible Spending Account (FSA) + Health Spending Account (HSA)
• 401k retirement plan
• Commuter benefits
• Discounted pet insurance

Our Philosophy

At Chicory, we know that we are strongest when every person is valued, respected and treated with dignity. We actively put aside assumptions and judgment and work to make space for all points of view. We do serious work but don’t take ourselves too seriously. We consider our playful spirit a competitive advantage to building better relationships and finding the smartest solutions. We produce the best results by hiring smart people and giving them the space, safety and the resources to do their work. We are building a company people love working with and working at.

Our Commitment Statement to Diversity, Equity, Inclusion, & Belonging

At Chicory, diversity, equity, inclusion, and belonging are key ingredients in our recipe for success. Our diverse experiences, backgrounds, identities, and ways of thinking elevate the level at which we operate; this allows us to innovate in old-school industries by looking not at how things have been done, but how they should be done. We are building a workplace built on merit and equity where every one of us has a voice at the table. 

Our Principles

• Be Good People: The success of our company is totally dependent on having good, smart people.
• Own It: We take pride in our work. When we see a problem, we step up. We hold ourselves, and each other, to the highest standard. We learn from mistakes, admit when we are wrong, and take full responsibility for delivering results, not just for our role, but for the mission.
• Separate Your Ego From Your Position: We speak up with conviction, but we stay open to being wrong. Leadership isn’t about winning arguments or defending turf; it’s about serving the mission. We challenge ideas without taking it personally, and we invite feedback without getting defensive. Our goal is the best outcome, not to “be right.”
• Find Reality: We pursue truth over comfort. We seek to understand before insisting on being understood. We dig beneath symptoms to uncover root causes, and we challenge assumptions, even our own. Clarity comes from curiosity, not certainty. We don’t settle for surface-level answers. We seek reality, even when it’s inconvenient.
• Have a Beginner’s Mind: Just because something has been done a certain way doesn’t mean it’s the best way. We stay curious, challenge assumptions, and question the status quo. We stay innovative by tackling problems from a fresh perspective.
• Bias for Action: Speed matters in business. We don’t wait for permission, perfect clarity, or endless alignment. We cut through noise, complexity, and politics to drive progress. When in doubt, we act, learn, and adapt because action beats indecision every time.
• Customer Obsessed: Our customers are our North Star. We listen closely, dig deep to understand their needs, and deliver 5-star service at every touchpoint. We build products that actually work: simple, intuitive, and designed to solve real problems.
• Above and Beyond: We don’t settle for “good enough,” we aim for exceptional. We go above and beyond what’s expected for our team, our customers, and ourselves. We stay curious and hungry. Every day is an opportunity to get better.