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Senior Manager, Sales Enablement

Washington, District of Columbia, United States

We created Upside to help communities thrive! Our retail technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick and mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cash back than any other product, and tens of thousands of brick and mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our local retailers, the consumers they serve, and towards important sustainability initiatives. Our mission, values, and commitment to inclusivity guide our team of more than 200 people worldwide, and the quality of our culture is reflected in the impact we’ve had on communities nationwide.


About the Job:

Upside is growing and is in search of an organized and ambitious Senior Manager on the Sales Enablement team, based in Washington, DC. You’ll join a Marketing Team whose experience hails from places as varied as Google, OPower, MasterCard Worldwide with proven startup executives and venture capitalists. This player/coach role is a unique opportunity to join a company that’s revolutionizing how personalized promotions can drive revenue for merchants in a scientific way. In this role, you’ll be responsible for growing and leading our Sales Enablement team. We are looking for competitive and hungry entrepreneurs who love technology and want to grow their career at a company looking to revolutionize local commerce.


What you’ll do:

  • Accelerate the performance of sales teams
  • Create plans for training and development of sales teams, including onboarding and role transfer
  • Continuously update training and onboarding based on data-driven performance insights and research
  • Facilitate enhanced cross-functional communication between sales and the teams that support them, such as various marketing teams
  • Implement sales strategy and work with Product Marketing to develop sales content and collateral that follow said strategy
  • Ensure systems are in place to allow for accessibility of content and information at time of need, updating systems and frameworks as needed (including maintenance and improvement of sales enablement platform / content management system)
  • Partner with Revenue Operations to develop methods that measure success of our sales enablement investments in content, tools, and methodologies
  • Collaborate with sales leadership to build and deploy sales plays that are tailored to each business vertical
  • Work cross-functionally with Marketing, Product, Operations, etc. to keep the Sales team informed and prepared in a climate of constant change
  • Build and lead a growing Sales Enablement team while focusing on continuous improvement, coaching, and career development
  • Occasionally identify gaps and necessary technical tools (with tech partners) to drive customer experience and revenue outcomes
  • Support creation and deployment of education materials to customers and partners


What you need:

  • 5+ years relevant experience either (a) directly selling or enabling people who sell B2B tech, SaaS, or PaaS in a company with at least 75 customer-facing roles, and/or (b) similar experience in a GTM consulting / advisory role
  • At least 3 years of people/team management experience, including coaching and career development (either through direct reports or as a leader of matrix programs)
  • Sales training experience preferred
  • Customer & partner training experience a plus
  • A deep understanding of the needs of a sales organization
  • Proven track record of scoping, building, and executing successful enablement programs, content, and integrated sales communications
  • Demonstrated operational rigor and project management experience working in fast-paced, high-growth environments
  • Experience working with sales tools including (Hubspot, ZoomInfo, LinkedIn Sales Navigator)
  • Excellent communication and influencing skills with the ability to motivate people
  • Experience building relationships and credibility with business leaders and executives
  • An adaptable and agile mindset that allows for new ways of thinking and solving problems


The fine print:

  • Notice to recruiters and placement agencies: This is an in-house search. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.


At Upside, we believe that diversity drives innovation. Our differences are what makes us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives and do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here, come join us!

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