Posted: Mar 28, 2021

Chief Revenue Officer

Application Deadline: N/A


In this newly created role, Dreambox’s Chief Revenue Officer will head sales strategy aligned with the evolving business strategy across current and future revenue streams. Reporting to the CEO, this leader will be a significant contributor to strategic business considerations, flipping between a functional hat and a business unit leader executive hat. The CRO will create a winning culture across the company, encouraging those outside of sales to feel they’ve had a part in each victory. This mindset of winning and business of selling not only answers to quarterly objectives but has the ability to see several years down the road. Crucial to success will be the ability to deeply understand the customer perspective and work hand in hand with the leaders of customer experience/success and product development to not only deliver what customers want but to envision solutions that do not yet exist.

The CRO will be a transformative leader with the ability to scale the organization, developing a state level go to market strategy while professionalizing the sales organization leading to overall growth. As an executive team member, and working with peers, this individual will drive to a highly integrated and collaborative outlook with regard to all go to market strategies. As the functional leader of the sales team, the CRO will guide and coach talent on the team; make accomplished talent better, drive career aspirations, create a harmony model while benefiting from leadership development provided to the executive team.

Primary responsibilities:

  • Grow recurring revenue and evolve sales organization as company matures with each new revenue marker (e.g. $100M, $200M)
  • Partner on inorganic growth exploration, advising especially on increasing addressable market and market share, sales organization integration, and cross-sell strategies
  • Evaluate and set compensation model in partnership with Finance and Human Resources
  • Use data to create and update a successful go to market strategy with regards to sales playbook and processes including evaluation of land and expand, hunter/gatherer, top-down, bottom-up, relational selling, volume-based selling, state deals, inside sales, and other sales philosophies
  • Assign territories, quotas, and partner with CFO to improve deal desk efficacy
  • Create sales training for existent and new products and services along with associated sales materials and route to market
  • Work closely with SVP of Client Success to increase customer retention and redesign sales strategy with regard to Professional Development services
  • Fully integrate the new data analytics product into a selling platform in need of overall upgrading

Ideal Candidate

The ideal candidate is not necessarily a current CRO, rather understands sales and sales sub-functions including finance, operations, sales ops, marketing, data and analytics. This individual has piloted a company through quick growth with a high functioning enterprise-scale sales team and a complex seasonal selling strategy. Past achievements have come from understanding that not all campaigns and offers are equal, sales outreach has been prioritized at different times with strategy around when to offer something free, at a discount, as a freemium, or when to hold value. An ability to work with product market fit and the courage to lean into ambiguity will help build a rolling 12–18-month view, and a team that understands how to hold value rather than defaulting to discounting.


You should have the following experiences and skill sets:

  • Expertise leading SaaS inside sales
  • Track record developing a strong sales team with a strategic outlook and cross functional mindset
  • Proven background navigating political sales involving 3-4 stakeholders with differing viewpoints, as well as the follow on to deepen customer relationships beyond purchase
  • Agility and versatility to adapt from one business model to the next
  • Strong background in B2B sales with understanding of B2C sales
  • Success in creating new revenue streams through meaningful partnerships
  • Difference between integration channel customers/brand consumers