Arena Careers

At Crooked, we believe the answer to a rising authoritarian movement is a democratic movement powerful enough to fight it and (fingers crossed) defeat it. That means using all the tools at our disposal as a media company to help build a massive, diverse coalition united behind a core set of democratic values: freedom, equality, compassion, and the rule of law.

Job Summary:

Crooked is hiring an Account Executive, Brand, Social & Live Sales Partnerships on the Sales team reporting to the VP of Sales. This role will focus on developing and closing high-impact partnerships with brands seeking cultural relevance, large-scale audience reach, and integrated storytelling opportunities across Crooked’s podcasts, simulcast video, social platforms, newsletters, and live events. This position will lead direct sales efforts with brand marketers and agencies focused on brand awareness, cultural moments, branded storytelling, social content and live experiences. The role will also help develop premium sponsorship opportunities tied to Crooked content and its tentpole events including Crooked Con, live tour programming, and special event coverage such as the White House Correspondents’ Dinner.

The ideal candidate will have deep relationships with holding company, brand, and agency decision makers, experience selling integrated media partnerships, and a track record of closing large multi-platform deals.

Crooked has adopted a hybrid work model for our entire staff. We believe that the best work is done in a hybrid capacity as it combines the flexibility of working from home with in-person collaboration. However, some positions at Crooked are remote for specific strategic reasons. And for this role it is based in New York with some travel required. We are ideally looking for New York based candidates or individuals are willing to relocate before their start date.

How You’ll Spend Your Time:

Direct Brand Sales

• Contribute to outbound sales efforts focused on brand marketers and agencies seeking upper-funnel awareness and cultural impact.
• Develop direct relationships with brand decision makers across marketing, partnerships, and brand strategy teams.
• Create proactive partnership opportunities that combine Crooked’s podcasts, simulcast video, social channels, newsletters, and live events.
• Package integrated campaigns that include host-read ads, branded segments, product and social integrations, and premium sponsorships.
• Own the sales cycle from prospecting through deal negotiation and closing.

Strategic Partnerships & Branded Integrations

• Develop large-scale sponsorship opportunities tied to Crooked tentpole events, including Crooked Con, live shows, cultural moments, and special programming.
• Lead the sale of branded podcast segments, sponsored editorial integrations, and custom storytelling opportunities across Crooked’s network.
• Identify opportunities for brands to participate in major editorial moments, breaking news coverage, and cross-platform storytelling.
• Develop sponsorship packages that combine podcasts, simulcast video, social distribution, and live experiences.
• Collaborate with programming and creative teams to design branded integrations that feel authentic to Crooked’s voice and audience.

Strategy & Client Management

• Serve as the primary point of contact for own brand partners and agencies across active campaigns.
• Work closely with Crooked’s account management, creative, and production teams to execute integrated partnerships across podcast, video, social, newsletters, and live events.
• Track performance, maintain strong client relationships, and identify opportunities to expand partnerships over time.
• Provide marketplace insights and advertiser feedback to inform Crooked’s sales strategy and future programming opportunities.

Operations

• Prospect, including the ability to qualify new leads and close new accounts
• Contribute to additional sales projects that require research, deck development or proactive response on a case-by-case basis
• Relay client and marketplace feedback and insights to better inform Crooked sales offerings, tentpoles and calendar initiatives
• Generate media plans and sponsorship proposals for podcasts, video, social, newsletters, and event integrations

What You’ll Bring To The Table:

• 7+ years of experience in media sales, brand partnerships, or integrated marketing
• Experience selling multi-platform media campaigns across audio, video, social, and live experiences
• Strong relationships with brand marketers, direct brands, and agency decision makers
• Experience developing and selling custom partnerships, branded segments, live event sponsorships, and social integrations
• Ability to create proactive partnership ideas tied to cultural moments and editorial programming
• Experience managing large deals and long-term strategic partnerships
• A collaborative mindset and ability to work cross-functionally with programming, production, creative, and ad operations teams
• Experience working with podcast or digital media platforms is strongly preferred
• Project management experience, with experience leading and handling multiple time-sensitive, cross-functional projects on deadline
• Must have previous presentation and client-facing experience in media
• Keen sense of confidence, ability to learn, and willingness to share knowledge learnings to teach the entire team
• Selfless team contributor willing to take ownership of tasks
• A positive mindset that values collaboration and delivering results
• Expertise in Microsoft Office Suite, with an emphasis in Excel, creating pitch decks (Google Slides/Powerpoint), and proposals (Google Sheets)
• Knowledge of Podcast Sales Software and Reporting (such as Simplecast, Megaphone, Podscribe)

This job description provides a summary of how you’ll spend your time but is nowhere near exhaustive, so other duties may be assigned over time.

Pay and Perks:

At Crooked, we believe in paying employees at market rates that are informed by salary surveys and industry benchmarks. In addition to competitive salaries, we offer full-time employees excellent benefits including:

• Paid healthcare
• 401k match
• Generous vacation and paid leave including, sick, bereavement, pregnancy loss, and disability leaves
• 20 weeks of paid parental leave
• Commuter reimbursement or paid parking
• Communications stipends
• Professional development opportunities
• Did we also mention our offices are closed at the end of the year?

Once we’re ready to extend an offer, we look at the individual’s years of relevant experience and other compensable factors to determine a competitive offer. And for this role, the salary range is $125,000-$145,000.