Head of Sales

Sorry, this job was removed at 08:17 p.m. (CST) on Thursday, May 29, 2025
Hiring Remotely in United States
Remote
Agency • Professional Services
Optimism is an inbox-first digital media company with brands that reach millions of Americans every day.
The Role

About Head of Sales

As the Head of Sales, you will lead and develop a high performing sales function to drive revenue. Your job is to level up our sales strategy, deepen our brand and agency relationships and drive meaningful scalable revenue across email and web.  You will be responsible for developing and executing a partnership sales strategyx.

You will be ready to pursue aggressive sales goals while simultaneously testing new approaches to our overall market positioning, and sales strategy, 

You are both seasoned and scrappy. You lead by example and are ready to both coach and roll up your sleeves and close big deals when needed,  iterating pitch and strategy across various customer segments - and then, from there, institutionalizing this approach into a playbook and systems for the team.

ACCOUNTABILITIES:

  • Build and create an external direct sales and partnerships strategy, which includes prospecting, pipelines, pitching, pricing, packaging, and closing.  Own the sales playbook to establish this growing team’s best practices for the whole funnel.
  • You need to be able to close key deals. Be on the front lines with the sales team and key clients, establishing the bar for what world class selling looks like. 
  • Understand the business objectives critical to our partners' success and align them with Optimism’s goals bringing continual innovation to our monetization strategies. 
  • Lead the direct sales function, top to bottom. Set the strategy, structure and process for scaling this function and team.
  • Work closely with the editorial team, business intelligence, sales ops and campaign teams to craft creative brand partnerships that perform.  
  • Continue to foster our internal direct sales channel by ideating and executing on the creation of ad products, capabilities, and functionality that external clients desire. Serve as our pulse on market feedback.
  • Keep abreast of industry trends and formulate shifts in forward-looking strategy
  • Lead strategic planning for Optimism’s brands function. Build and manage the sales team’s pipeline, deliver accurate revenue forecasts and goals and report on KPIs regularly. 
  • Act as a cultural champion for rigor, curiosity, inquisitiveness, and a performance mindset.

Requirements
  • 10+ years of experience in digital publishing sales with 5+ years leading a high performing sales team
  • Experience selling. Demonstrated capacity to prospect and qualify lead and close deals, with strong focus on direct partnership with DTC brands and agencies
  • Track record of exceeding sales goals in exceeding revenue targets and scaling high-performing sales team 
  • Experience selling both email and web media properties, across a network of brands in various verticals and proven ability to build large integrated campaigns for clients.
  • Bring an existing warm rolodex of relevant media buyers with key decision makers at both brands and agencies.
  • Strong interpersonal skills, proven negotiation skills and a relentless drive to achieve results.
  • Excellent team management and coaching skills.
  • Ability to synthesize data and help others make data-driven decisions
  • Strong organizational skills and high level of attention to detail.
  • Be able to work cross functionally with many other roles and stakeholders in the company
  • Entrepreneurial spirit, strategic thinker, strong desires to DRIVE revenue, ability to execute in an ever changing fast paced environment and a thirst for learning.

While this position may be remote, we prefer candidates who can work in Orange County, Denver, or New York City.


Benefits

This role offers in all in compensation package between $350-375k plus an extensive benefit package.

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The Company
HQ: New York, New York
20 Employees
Year Founded: 2021

What We Do

Optimism's portfolio consists of more than a dozen publications spanning a wide variety of topics. While the subject matter may vary (from travel to learning to news) all of Optimism's brands are united by a singular mission: to build a brighter web. This mission carries through to each and every one of Optimism's brands, all of which at their core aim to be nourishing and uplifting to their readers. This promise has allowed Optimism to build a powerful audience of millions of engaged subscribers who have made a habit of starting their day with Optimism.

Why Work With Us

Working for Optimism will expand your skill set and drive your curiosity, as it embodies and supports multiple different trades such as art, creative ventures, content and strategic investments. You will be treated like family and immersed in a culture of connectedness while fostering your personal and professional growth.

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