Our Vision

At Retrospect, our vision is to build the safest and freest space for marginalized people and social outcasts to practice self-love and joy. We want to curate an environment for makers form all backgrounds to be able to create at the intersection of innovation and culture.

Work with Us

We’re looking for generalists and specialists. Career shifters, and planned it out since you were young. Whatever your background is, we invite you to see if we might be a match for you. 

The role:

As the Head of Sales for Retrospect, you oversee and manage the day-to-day relationships with our clients. In this highly dynamic role, you will help shape our Sales organization and how our products and services are marketed to clients by driving innovation, challenging existing methods, and defining requirements to drive YOY growth. As one of the early-stage members of the team, you'll have the opportunity to make an outsize impact beyond the traditional scope of a sales/marketing/product role. We know it's a big ask - so we'll work collectively as a team to get the work done. 

Candidates must have experience in the creative, marketing, tech, or advertising agency industries. You will work cross-functionally across marketing, account management, and product to ensure strong and consistent messaging across all customer touchpoints.  

What you'll do:


  • Responsible for leading and managing the Sales organization at Retrospect
  • Market and sell through Retrospect services to large enterprise clients
  • Help to define and support SMB deals
  • Serve as the senior lead on client business and oversee all aspects of the assigned LOB(s), working closely with internal teams to craft a strategic POV for clients' business goals
  • Ensure continued revenue growth, effective brand positioning, innovative operating systems, and performance reporting 
  • Maintain an active pipeline of 20+ clients in our CRM (Hubspot) and lead weekly Deal Desk meetings
  • Lead and guide new business pitches in partnership with cross-functional teams (Design, Strategy, etc.) 
  • Grow accounts with exemplary client service, delivering on business, strategic and creative goals
  • Establish and maintain trusted relationships with key decision-makers in client and agency organizations
  • Foster and maintain a vast network of valuable relationships in key business sectors to attract viable business opportunities
  • Ability to unlock and activate prospective opportunities through our existing networks and our agency partners 
  • Demonstrate exceptional organization and attention to detail to build a framework for identifying opportunities, prioritizing and managing client deals, and scoping projects to ensure profitability/ROI goals are achieved
  • Incorporate the messaging, positioning, and GTM strategy for our team and clients in our overall Sales strategy
  • Shape and develop product positioning, value propositions, and messaging to be used in product development and marketing campaigns for Retrospect and our clients
  • Track, analyze, and communicate Retrospect sales outcomes and opportunities to leadership, including the development of quarterly and annual sales plans
  • Maintain awareness of news and key market trends that impact client account/s and our opportunities in the creative and tech industries


  • Build, manage, and develop a team that drives the success of Retrospect and its offerings while fostering a culture that encourages creative thinking and collaboration
  • Strategic partner and driver for headcount planning 
  • Strategic partner in the development of internal and external marketing strategies and experiences that help drive brand awareness for Retrospect  
  • Act as a brand ambassador and thought leader for Retrospect in industry and public forums

Who we are looking for:

  • Experienced & tenured Sales / Account/ Marketing leader (with at least 3 years of leadership experience) 
  • Have extensive experience with Full funnel sales ( pre-sales to post-sales)
  • Strong understanding of advertising, marketing, creative, and media fundamentals such as scoping, pricing analysis, and executing go-to-market strategies and campaigns
  • Proven track record of driving prioritization of key sales and growth initiatives through an established framework
  • Strong business acumen, negotiation, client, and revenue management skills
  • Experienced in attracting and winning new business
    • Proven ability to maintain and grow existing client relationships
    • Proven ability to attract new account (s)
    • Has managed and delivered against P&L, revenue models, and quotas
  • Previously started up or led a new team
    • An organizational leader with a passion for building dynamic teams 
    • Has managed 3-5 direct reports/ team pod(s)
    • Proven track record of leading diverse teams
  • Excellent time management and prioritization skills 
  • Problem-solving skills, with the ability to come to rigorous and defensible solutions to complex and open-ended problems
  • Strong strategic thinker with the ability to access and provide actionable recommendations based on data and trends
  • Strong quantitative and analytical skills with experience managing data flow across multiple sources
  • Strong understanding & ability to quickly learn the creative process and design sprints across core capabilities 
  • Comfort partnering with central creative and marketing teams to build marketing campaigns, providing thought leadership and industry POV
  • Strong written, verbal, and copywriting skills.
  • A customer-first approach with a passion for storytelling

Benefits & Perks:

  • Opportunity to work in a fast-paced start-up environment with experienced industry leaders
  • A learning environment where you can dive deep into the latest technologies and make an impact
  • Competitive salary and equity
  • Company-sponsored medical, dental, and vision insurance 
  • 401k (with match) and paid parental leave
  • Unlimited vacation policy

The annual base pay range for this role is between $120,000.00 - $140,000.00

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