Head of Sales

About Us

Right Side Up is a collective of premium marketing talent—with all of the marketing chops, and none of the agency fluff. We’re trusted by the most buzzed-about early-stage ventures, the fastest growing tech companies, and well-established Fortune 500 teams to do one thing better: GROWTH.

Some of our clients include Robinhood, Yahoo!, Reddit, Waymo, Gusto, Boulevard, Coinbase, Doordash, among many others.

The Role

We are looking for a sales leader to stand up our outbound sales function and apply sales best practices to our team of marketing leaders who field inbound leads (“Project Strategy”). In this role, you will be a vital member of the leadership team, guiding how we effectively find new prospective clients and persuade them to choose us, across a wide variety of industries, stages, and business needs. You will work closely with our marketing team on collateral, case studies, and other content initiatives. This is both a strategic and hands-on role that is perfect for someone with depth in sales and go-to-market team leadership, with a keen focus on building and scaling best in class revenue teams. This role does not, at least initially, include oversight of our efforts to cross-sell and upsell our active clients.

• Define, implement, and evolve the go-to-market and sales strategy.
• Build and manage the full sales funnel from lead generation through close.
• Develop KPIs and sales metrics to track performance and identify improvement opportunities.
• Own the revenue target and pipeline; forecast accurately and meet or exceed revenue goals.
• Represent the company in high-stakes client meetings and pitch opportunities, cultivating long-term relationships with contacts at strategic prospects.

• Hire, train, and mentor a high-performing outbound sales team.
• Manage our 14 person Project Strategy team towards excellent consultative selling.
• Set performance expectations and foster a culture of accountability, collaboration, and success.
• Leverage the team’s marketing expertise and ensure we always transparently tell clients when they should not hire us. 
• Collaborate with delivery and client success teams to ensure smooth handoffs and client satisfaction.
• Provide feedback to internal teams to enhance service offerings and client value.
• Work closely with marketing, client growth, and client success to ensure strong lead generation and nurturing programs.

• 7–10+ years of B2B sales experience, with at least 3–5 years managing a high performing team.
• Proven success in selling fractional marketing talent, agency offerings, or consulting solutions through cold outreach (email, phone, and/or LinkedIn).
• A rolodex of CEOs, CMOs, and VPs of Marketing that gets us in the room with valuable prospects in the first 60 days. 
• Track record of hitting and exceeding revenue targets in a service-based business that leans heavily on consultative / strategic selling. 
• Success standing up a successful outbound sales team from scratch.
• Ability to apply frameworks, tools, and structured programs to optimize the performance of an inbound sales team.
• Strong written and verbal communication skills — able to conceptualize and communicate strategy clearly and compellingly.
• Comfort operating in a high-growth, ambiguous, and fast-moving environment.
• Expert with CRM tools (ex: HubSpot, Salesforce) and outbound/prospecting tools (ex: LinkedIn, Clay).
• Intermediate to advanced understanding of digital marketing, growth marketing, or performance marketing.

• After 30 days: You’ve built rapport with the Project Strategy team, understand our value props, are kicking off outbound campaigns, and we’re setting up conversations with 5 contacts from your rolodex to pitch. 
• After 60 days: You are coaching direct reports, communicating and measuring your goals with the team, driving consistent calls from outbound sales efforts, and able to effectively pitch Right Side Up to VIP CMOs on your own. 
• After 90 days and beyond: You're fully ramped up in the role and have shown success unlocking outbound sales opportunities that are aligned with our target ICP. You’ve implemented new processes and tactics to increase conversion rate from lead to customer. You're fully integrated with your direct team, and partnering closely with cross functional stakeholders to advance progress against our sales/revenue growth goals.

• A leadership role at an innovative, high-growth company at the forefront of marketing with the best brands in America. 
• Management of a large, high-performing team of marketers fielding inbound leads.
• A collaborative, inclusive, and fun remote-first culture. Competitive compensation package.
• Full suite of benefits, including health, dental, vision, and flexible paid time off.