Job Description

SENIOR SALES DIRECTOR – Enterprise Sales (Player Coach)

JOB TITLE: Director or Vice President of Sales

LOCATION : San Diego, CA; On-Site ; Full Time

To Apply: Send a Cover Letter and Resume to [email protected]

TOOTRiS is a rapidly growing, software-driven childcare benefits provider. We empower enterprise organizations across diverse industries—including manufacturing, healthcare, technology, government and finance—to offer turn-key childcare solutions to their employees. TOOTRiS streamlines the management of these benefits through our innovative technology, assisting parents in using their employer-sponsored benefits with child care providers nationwide.

With over 230,000 providers nationwide in our network, TOOTRiS is the largest and only platform that provides real-time access to state licensed and registered Child Care providers in all 50 states today where parents can search, vet, book and pay for Child Care services – 24x7!  We're transforming the world of childcare by making it more convenient, affordable, and accessible for working parents. Our platform helps companies increase employee retention and productivity while providing valuable benefits that support working families. As digital solutions increasingly shape our lives, TOOTRiS enables real-time connections and transactions between parents and child care providers. Our platform empowers working parents – especially women – to find high-quality child care effortlessly, while helping providers enhance their offerings and fully capitalize on their programs.

We are in search of a dynamic leader to take our enterprise sales to the next level using past experience and industry knowledge to build and lead a team of Sales Executives and Account Managers. This person will bring with them the lessons learned from past wins and losses and the hunger to exceed expectations leading by example… If that’s you, we invite you to apply and be an integral part of our dedicated team committed to excellence.

Position Overview:

TOOTRiS is seeking a dynamic and results-oriented Senior Sales Director to lead and significantly grow our Enterprise Sales team . This individual will be a strategic leader with a proven ability to drive revenue through the acquisition of large enterprise clients.

This is a critical leadership role focused on building and managing a high-performing enterprise sales organization. The Director will be responsible for developing and executing sales strategies, managing key client relationships, and acting as a strategic liaison between enterprise clients and internal TOOTRiS teams. This role will also encompass a player-coach dynamic , requiring the Director to both lead the team and actively engage in direct sales activities, including managing key accounts and driving significant deals to closure.

The ideal candidate will have a demonstrated track record of building and leading successful enterprise sales teams, consistently exceeding sales targets, and penetrating complex enterprise accounts. This role requires a strong understanding of enterprise sales cycles, exceptional negotiation skills, and the ability to build and foster long-term, strategic partnerships with key decision-makers within large organizations. The Senior Sales Director will be instrumental in driving TOOTRiS's growth within the enterprise market, both through strategic leadership and direct sales contributions.

RESPONSIBILITIES:

· Lead and build a high-performing sales team from the ground up, nationally, expanding to a substantial workforce. Utilize your extensive SAAS sales experience and relationships to enhance the national footprint.

· Implement and refine end-to-end sales processes, utilizing a hands-on and scientific approach to building a robust pipeline. Execute strategic account plans to drive success and foster long-term partnerships.

· Act as a dedicated advocate for clients within our organization, ensuring seamless communication, effective resolution of issues, and a consultative approach to understanding clients' evolving needs.

· Provide formal training on sales processes, leveraging your expertise to mentor and guide the team. Utilize your relationships and experience with SAAS sales across industries.

· Develop and implement strategic plans to maximize the impact of our Child Care solutions, aligning seamlessly with clients' goals and contributing to the well-being of working families.

REQUIRED EXPERIENCE:

· Sales Experience:

o Minimum of 3 to 5 years of hands-on experience in SAAS or benefits sales.

o Proven track record of achieving and exceeding sales targets.

· B2B Sales:

o 3+ years of dedicated experience in B2B sales .

· Leadership Experience:

o Success in building a team of experienced professionals , fostering a collaborative and high-performing sales environment

o Previous experience leading a team of at least 5 with a national footprint

· A leadership style that values autonomy, enabling team members to excel independently.

· A hands-on and scientific approach to crafting and executing sales pipelines, ensuring a methodical and data-driven strategy.

· Proven ability and willingness to personally engage in sales activities, stepping in when needed close deals to achieve organizational objectives.

PREFERRED EXPERIENCE:

· Previous familiarity with the Benefits and/or Insurance industry.

· Understanding of the unique challenges and opportunities in the child care sales landscape.

· In-depth knowledge of the Child Care business landscape and regulatory environment.

· Prior experience as a client advocate, ensuring effective communication and issue resolution.

o Familiarity with innovative solutions that align with business objectives in the context of Child Care services.

· Familiarity with Salesforce or similar CRM tools.

· Formal training in advanced sales processes, including recognized programs such as Miller Heiman Training, demonstrating a commitment to excellence.

BENEFITS:

· $125K-$165K Base Salary DOE

o $275K+ OTE (uncapped) earning potential as sales team grows

o Bonus structure, Stock Compensation, with residuals from sales team

o (Full compensation package to be discussed on per person basis)

· Child Care

· Medical, Vision, & Dental Insurance

· Unlimited PTO *after 120-day cycle*

· 11 Holidays AND Birthday off

· 401K plan

· Equity/Options

· Full benefits & stock package to be discussed on a per-person basis

Important Details

TOOTRiS is Committed to creating an environment where employees thrive. It's why we provide every employee with unlimited PTO as of your 120 th day of employments, private health insurance, and a 401K plan and of course, Child Care as a Benefit 😊. New employees will go through an intense 3 day new-hire bootcamp, which customizes the onboarding experience by role, provides new employees with invaluable hands-on training within their first few days at the company, and gives employees the chance to meet their new colleagues in-person.

TOOTRiS is an Equal Opportunity Employer, and we believe that every employee in the company brings a unique perspective that they can and should contribute in order to make an impact every day. We strive to be one team, one culture, and one family that builds trust through transparency. We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity, age, national origin, protected veteran status or disability status.

Please send resume information to: [email protected]

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