Director of Sales (Remote)

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*This position is eligible to be hired virtually within the US or locally in Atlanta, GA 

At Cypress.io, we're on a mission to make software testing delightful and effective and thus dramatically improve the efficiency and quality of modern software development. Today, Cypress provides better, faster, and more reliable testing for anything that runs in a browser. Hundreds of thousands of developers and QA professionals use Cypress to write better code faster and release with confidence.

Cypress is currently used in over 90 countries by hundreds of thousands of developers across more than 30,000 organizations. Cypress has over 2,500 customers in more than 60 countries across 45 industries and includes marquee names like Atlassian, Crunchbase, GitHub, PayPal, and Slack.

The company was founded in 2015 and has raised $55M in capital to date, including a $40M Series B financing in November 2020, led by OpenView Partners, with participation from Bessemer Venture Partners, Battery Ventures, Sapphire Ventures, and Stripes.co.


The Head of Sales role is an innovative opportunity to lead the Cypress Sales organization. 

Leading our mid-market and strategic sales teams, you will build to support our evolving GTM model. The right candidate should have strong experience selling in a bottoms up PLG sales motion, bringing strong methodology and best practices to sell a SaaS product aimed at developer audiences. 

The Head of Sales will report to the VP of Sales and Success, and is charged with new and expansion revenue in our managed sales efforts. They will implement new business processes to support our evolving GTM model. The Head of Sales should have strong knowledge of the sales process, methodology, and best practices to sell a SaaS product aimed at developer audiences. They should be comfortable bringing structure to ambiguity, prioritizing in a high opportunity environment, and demonstrate the ability to lead boldly in rapidly changing conditions.

Our GTM focuses on a bottoms up approach. Our open source developer product, strong community partnership, and developer friendly approach means our customers already have strong engagement with our product and framework. Our sales motions drive greater expansion and adoption. 

This role will be responsible for revenue, creating the appropriate team structure, sales playbooks and strategies, and hiring and developing the best team possible. They will work closely with Marketing, Revenue Operations, Product, and Customer Success teams to drive GTM motions including strategy, messaging, process, documentation, tooling, account management, training, etc.


Role Overview:

  • Own team revenue contribution goal
  • Lead strategic and mid market teams directly or through first and second line leadership
  • Own department performance and accountability
  • Develop and document process and procedures, and drive adherence to them in order to build scalable motions for investment
  • Develop leadership within the sales organization that extends the capacity of the team and drives excellence in the organization
  • Deliver forecasts, reporting, and updates to leadership and company
  • Partner cross functionally with Marketing, Customer Success, Revenue Operations, Product, and Engineering to drive better product delivery and better engagement with our customers and prospects
  • Establish predictable and repeatable sales motions

During your first year your role will be broad and include:

  • Building out and hiring for the Sales team
  • Coach, mentor, and manage future sales leadership to progress and grow in their careers and at Cypress
  • Develop playbooks and process that enable performance and success
  • Leverage data to critically think through ways to grow, optimize and impact the team
  • Think of the Sales team as an input for marketing and product development that ultimately drives better product delivery and better engagement with our customers and prospects 

Experience:

  • Leadership: previous experience in a Sales leadership role demonstrating resilience, accountability, inclusion, and agility preferably during early growth stages of a company where the team and business is in create and build mode.
  • People Management: strong, intentional, and inclusive people management, managing Sales professionals from diverse backgrounds for teams of over 10+ folks
  • Hiring: Growing and hiring teams directly through equitable, established and thoughtful hiring practices
  • Product-let Growth: GTM motions with a PLG lens take on a different cadence, interaction, and strategy, having worked at a Product-led growth company would give you fantastic analogous experience
  • Cross-functional Partnership: Extensive collaboration with leaders and team members within Marketing, Revenue Operations, Market Development, Customer Success and Product Management to execute and succeed together 
  • Market Segment: SMB and Enterprise sales experience
  • Customer/User: Compassion and empathy, paired with experience for developer/technical users and customers. 

Talent Attributes - what we look for in all hires at Cypress

  • Self awareness: you seek to understand your own behaviors, actions, emotions and traits in an effort to continually improve and develop.
  • Collaboration: you work together towards a shared goal, not in service of individual needs.
  • Stage Appropriateness: you have experienced growth and scale and understand the impact it has on individual roles, decision making, prioritization and our vision.
  • Intrinsic Motivation: you are driven by an internal desire to achieve, succeed and contribute
  • Intellectual Curiosity & Agility: you have a perpetual need to learn new information, and with exposure to it you’re able to adopt and modify your thoughts, solutions and outcomes.

#LI-Remote

Although we list out what we generally look for, we are very likely missing other attributes and skills that you have that could make you a great fit, and are not currently listed. Research has shown this especially applies to women and other marginalized groups, who tend to apply if they check 100% of every box, versus men who apply if they hit roughly 60%. The point we’re getting at, it doesn’t hurt to take a chance and apply!

We are an inclusive employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

More Information on Cypress.io
Cypress.io operates in the Software industry. The company is located in Atlanta, GA. Cypress.io was founded in 2015. It has 131 total employees. To see all 6 open jobs at Cypress.io, click here.
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