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Vice President, Sales

About Cleo:

At Cleo, we make a real impact by doing work that matters: helping families be their best at home and at work.


Cleo is the leading family benefits platform that picks up where the healthcare system leaves off. We combine the expertise of our team of Guides and Specialists—parent, maternity and adult care coaches, doulas, lactation consultants, sleep experts, and more—with a powerful technology platform that helps every working caregiver succeed.


Cleo is offered by over 200 leading employers, including global Fortune 500 leaders and industry innovators like Salesforce, PepsiCo, The Learning Care Group, Red Bull and Pinterest. With $81M raised from top investors including NEA, Greylock, and Transformation Capital, we’re expanding our offerings and our team to meet the growing demand of employers, caregivers, and the healthcare sector. Now we're looking for experienced and passionate team members like you to join us.


Title: Vice President, Sales


Overview:

As the Vice President, Sales, you will be responsible for hiring, developing, motivating & managing the Sales, outsourced BDR and Consultant Relations teams to meet and exceed Cleo’s business growth targets. In a player/coach role, you will also be responsible for achieving your own quota. You will use your passion for employer benefit sales and healthcare to balance result driven goals while building a positive team culture to align with Cleo’s values. This role reports to the SVP, Commercial and Growth.


As the VP, Sales you are a consultative seller who is passionate about working with decision-makers to support their employees and families. You are goal-oriented and resourceful, making strategic decisions to drive the sales pipeline and drive conversion to deliver said goals successfully. You understand the employer health and benefits sales cycle, and are skilled at managing all stages of the sales pipeline process. You have demonstrable success in working with brokers, consultants, and partners. You are a leader and a coach for your team, digging into details and strategies to position and advance sales opportunities.  You know how to utilize data and focus on the right behaviors to move the organization's results forward.


Key Responsibilities
  • Set a vision and purpose; develop and implement a comprehensive sales strategy focused on driving revenue growth and market expansion
  • Lead, coach and mentor the Sales, BDR & Consultant Relations teams to sell Cleo to employers and health systems
  • Cultivate a strategic, results-driven sales organization 
  • Provide hands-on leadership and professional development; ensure the team is motivated, aligned with our goals, and developing
  • Establish clear goals, measurements, and performance metrics. Analyze patterns and define data-driven strategies to optimize business performance across the entire team
  • Provide full visibility into the sales pipeline at every stage of the deal, with detailed knowledge of the key opportunities and accurate forecasting
  • Provide leadership and support on sales proposals, presentations, pricing and contract negotiation
  • Provide subject matter expertise and assist the team with strategy and actions plans on complex deals
  • Develop strategic sales and consultant relations plans based on company goals to promote growth and customer satisfaction
  • Provide candid feedback on the product suite, value proposition, and messaging resources at your disposal to drive improvement and refinement
  • Work cross-functionally on Cleo’s commercial leadership, product, operations, legal, and finance teams to achieve sales and organizational goals
  • Stay current with changes and developments in the employer benefits and healthcare industry
  • Scale the enterprise sales team as we grow, hiring top talent and ensuring the team is aligned with our goals


To be successful in this role you may have:
  • 7+ years of proven senior sales leadership experience in exceeding team and personal quotas
  • Successful bac
  • Strong background in selling employer benefits or other HR solutions to large enterprise (Fortune 500) clients
  • A robust rolodex of benefits leaders, consultants, brokers, and other industry influencers
  • Strong leadership abilities and an innovative, entrepreneurial attitude
  • Sales management experience in an early stage, high growth VC backed company (preferred)
  • Strong analytical and quantitative skills and the ability to think strategically
  • The ability to work in a dynamic environment where you will need to make quick decisions or shift priorities to drive growth
  • Demonstrated success in B2B enterprise and large company sales delivering client-focused solutions based on customer needs
  • Demonstrated ability to communicate, present, and influence credibly and effectively at all levels and cross-functionally
  • Experience working across multiple channels with consultants and brokers
  • A proven ability to manage multiple projects at a time while paying strict attention to detail
  • Experience with sales processes, CRM tools, and sales analytics to guide informed decision-making.
  • Effective verbal and written communicator; ability to distill complex information and messages to a broad and diverse audience.
  • A positive attitude that is flexible and open to change


#LI-Remote

We don’t believe in perfection – we believe in passion, interest, and will – so don’t let a lack of experience or skill in one area listed above deter you from applying.


Cleo is proud to be an Equal Opportunity employer. We highly encourage people of any race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.


Pay Transparency:

The base salary for this position is $210,000 annually plus a variable compensation plan. In addition to salary, Cleo offers the following benefits: health insurance (medical, dental, and vision), 15 paid holidays, 5-day winter break, flexible vacation time, sick time, 16 weeks paid parental leave, 401(k) plan, disability insurance, life insurance, wellness perks, and more.


Cleo is currently accepting applications from candidates residing in the following states: California, Colorado, Connecticut, Florida, Georgia, Illinois, Massachusetts, Maryland, Minnesota, New Jersey, New York, North Carolina, Oregon, Pennsylvania, Rhode Island, Tennessee, Texas, Utah, Virginia, Washington, Wisconsin.


SF FAIR CHANCE ORDINANCE

Pursuant to the San Francisco Fair Chance Ordinance, Los Angeles Fair Chance Initiative for Hiring Ordinance, and any other state or local hiring regulations, we will consider for employment any qualified applicant, including those with arrest and conviction records, in a manner consistent with the applicable regulation.

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What You Should Know About Vice President, Sales, CLeo

At Cleo, we're on a mission to support families by redefining how they engage with their benefits. We're searching for a Vice President, Sales to join our passionate team. In this remote position, you'll play a pivotal role in hiring, developing, and leading our Sales, outsourced BDR, and Consultant Relations teams to ensure we exceed our business growth targets. Your prior experience in sales leadership within the employer benefits or HR solutions space will shine as you embrace a player/coach role, actively pursuing your own sales quota. You'll leverage your passion for healthcare and employee benefits to foster a results-driven yet nurturing team culture that aligns perfectly with Cleo's values. Reporting directly to our SVP, Commercial and Growth, you’ll create and implement strategic sales plans focused on market expansion and revenue growth. Your ability to coach and mentor your team will be essential in helping them align with our organizational goals. We believe in providing clear visibility into the sales pipeline, ensuring accurate forecasting, and developing strong relationships across brokers and consultants. To be successful, you should have over 7 years of senior sales leadership experience and a robust network of industry contacts. At Cleo, we value passion and interest over perfection, and we believe that every team member adds unique value to our mission. If you’re ready to lead an innovative sales organization from a remote location and help make a significant impact on the lives of families, we’d love to hear from you!

Frequently Asked Questions (FAQs) for Vice President, Sales Role at CLeo
What qualifications do I need for the Vice President, Sales position at Cleo?

To excel as the Vice President, Sales at Cleo, candidates should have at least 7 years of senior sales leadership experience, particularly in the employer benefits or HR solutions sectors. A demonstrated record of exceeding sales quotas coupled with a robust rolodex of industry contacts will be essential. Proven leadership skills and strategic thinking are key to driving the sales team's success.

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What are the responsibilities of the Vice President, Sales at Cleo?

As the Vice President, Sales at Cleo, you will lead and develop the Sales, BDR, and Consultant Relations teams. Your responsibilities include setting clear sales strategies, mentoring your teams, achieving personal sales quotas, and ensuring alignment with company objectives. You will analyze sales data, forecast accurately, and collaboratively work across departments to drive organizational success.

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How does the Vice President, Sales role at Cleo contribute to company culture?

The Vice President, Sales at Cleo plays a crucial role in shaping and nurturing a positive team culture. By balancing results-oriented goals with supportive coaching and mentorship, this position helps create an environment where team members are motivated and aligned with Cleo’s values. Your leadership will foster collaboration and innovation within the sales organization.

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What experiences are best suited for the Vice President, Sales role at Cleo?

Ideal candidates for the Vice President, Sales role at Cleo should have extensive experience in B2B enterprise sales, particularly within large Fortune 500 companies. A strong background in the healthcare or employer benefits sectors is critical, as well as the ability to navigate complex sales cycles and manage relationships with brokers and consultants effectively.

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What benefits does Cleo offer for the Vice President, Sales position?

Cleo offers a competitive salary of $210,000 annually for the Vice President, Sales position, along with a variable compensation plan. Additionally, we provide comprehensive health insurance, 15 paid holidays, flexible vacation time, 16 weeks paid parental leave, 401(k) options, and various wellness perks, ensuring our team members are well supported.

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Common Interview Questions for Vice President, Sales
How do you plan to drive sales growth as Vice President, Sales at Cleo?

To drive sales growth at Cleo, I would establish a clear vision and comprehensive sales strategy tailored to the market. Involving the team in honing our value proposition would also be crucial, aligning their strengths with organizational goals and utilizing data-driven insights to inform decision-making.

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Can you describe your experience with consultative selling?

My experience with consultative selling revolves around understanding client needs and fostering relationships. By positioning myself as a trusted advisor, I ensure that the solutions presented are tailored to meet the unique challenges of our clients, which in turn builds loyalty and fosters long-term partnerships.

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What strategies do you use to motivate and manage your sales team?

I focus on building a positive, collaborative environment where team members feel empowered to express their ideas and challenges. Regular one-on-one coaching sessions, clear performance metrics, and recognizing individual and team achievements are key strategies I implement to keep motivation high.

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How do you handle challenging negotiations with clients?

During challenging negotiations, I prioritize open communication and understanding the client's perspective. I aim for a win-win outcome by being transparent about our capabilities while remaining firm on our value proposition. Utilizing a consultative approach allows me to build rapport even in difficult discussions.

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What is your approach to forecasting and managing the sales pipeline?

My approach to forecasting involves regular analysis of sales metrics to accurately predict revenue. I ensure the sales pipeline is transparent, monitoring key opportunities and stages closely. This meticulous tracking helps me provide timely insights and adjust strategies to maintain momentum.

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How do you incorporate data-driven strategies in your sales process?

In my sales process, I leverage analytics to understand patterns, assess team performance, and identify opportunities for improvement. By analyzing data, I can adjust sales tactics or coach team members more effectively, ensuring our overall strategy is agile and responsive to market demands.

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What experience do you have working with brokers and consultants?

I have extensive experience collaborating with brokers and consultants, where I build relationships and educate them about our offerings. Through active engagement, I obtain valuable insights that help tailor our proposals to meet the needs of potential clients effectively.

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How do you stay updated on industry trends in healthcare and employer benefits?

I stay updated by actively participating in industry events, engaging with thought leaders, and subscribing to relevant publications. This ongoing learning ensures I can offer valuable insights to my team and our clients while adapting strategies to align with market changes.

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Can you provide an example of a successful sales strategy you've implemented?

One successful sales strategy I implemented involved creating customized pitch sessions for different segments of our target market. By analyzing the needs of each segment, I could tailor our approach and messaging, resulting in a significant increase in conversions and revenue within that year.

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Why do you want to work as Vice President, Sales at Cleo?

I am drawn to Cleo's mission of supporting families and addressing gaps in the healthcare system. The opportunity to leverage my sales expertise in an organization that prioritizes meaningful work aligns perfectly with my values, motivating me to contribute to both the growth of the company and the well-being of families.

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Cleo, a Canadian specialty brand specializing in women's workwear in regular and petite sizes, proudly supports The Breast Cancer Society of Canada, having raised over $3 million.

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Full-time, remote
DATE POSTED
January 9, 2025

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