Inside Sales Executive

Overview

You sell advertising solutions across iHeartMedia's radio stations, podcasts, streaming platforms, and live events to businesses in the St. Petersburg/Tampa market. Your day is spent cold calling local businesses, following up on leads, presenting media plans, and closing deals that range from a few thousand to $50K+ annually. You're working with small business owners and local marketing managers who are evaluating radio against digital, TV, and other local advertising options.

Role Snapshot

Company Context

Stage: Public company (emerged from bankruptcy in 2019)

Size: 12,604 employees

Growth: Traditional radio revenue declining industry-wide, but iHeart is expanding into podcasts, streaming, and digital attribution

Market Position: Market leader in traditional radio with 90% monthly US reach, competing to stay relevant as ad dollars shift to digital platforms

GTM Reality

Pipeline Sources:

• 30% Inbound - business owners calling in after hearing ads, previous clients renewing, basic web leads (quality varies widely)
• 60% Outbound - you're making 40-60 calls per day to local businesses, working through lists of prospects in your territory
• 10% Referrals/Walk-ins - occasional referrals from existing clients or businesses reaching out after events

SDR/AE Structure: No dedicated SDRs - you source your own pipeline and close your own deals

SE Support: No sales engineers - you present media plans yourself, may get support from a marketing solutions consultant for complex packages

Competitive Landscape

Main Competitors: Other local radio groups (Audacy, Cumulus, Beasley), local TV stations, digital platforms (Google Ads, Facebook/Meta, Spotify), outdoor/billboard companies, streaming audio (Spotify, Pandora)

How They Differentiate: Massive reach (90% of Americans monthly), integrated cross-platform solutions (radio + podcast + streaming + events), proprietary attribution/analytics tools that track ad effectiveness

Common Objections:

• "Radio is dying, everyone listens to Spotify now"
• "Your rates are too high compared to digital"
• "I can't track ROI like I can with Google Ads"
• "My customers are online, not listening to the radio"

Win Themes: Local market dominance, reach scale that digital can't match for certain demographics, brand awareness building, combined audio+events packages, attribution data showing conversions

What You'll Actually Do

Time Breakdown

Prospecting/Calling (40%) | Active Deal Management (35%) | Admin/Internal (25%)

Key Activities

• Cold calling local businesses: You're dialing 40-60 businesses per day - restaurants, car dealerships, healthcare practices, retail stores. Most don't pick up. You're trying to book 8-12 discovery meetings per week.
• Building media plans: When you get interest, you create custom advertising packages across radio dayparts, podcasts, streaming, maybe event sponsorships. You're matching their budget to the right mix of reach and frequency.
• Closing deals: Walking prospects through proposals, handling pricing negotiations, getting contracts signed. Deals under $10K often close in 1-2 calls. Larger annual contracts require multiple stakeholders and 4-6 weeks of back and forth.
• Account management: Once a campaign runs, you're checking in on results, addressing complaints ("I didn't hear my ad" or "I'm not seeing sales lift"), and trying to upsell additional flights or renew annual contracts.

The Honest Reality

What's Hard

• Radio has a perception problem - many prospects think it's outdated or can't compete with digital targeting. You spend a lot of energy overcoming "Is radio still relevant?" objections.
• You're competing against businesses' entire marketing budget, including digital channels that offer easier tracking. Proving ROI is harder than with Google Ads.
• High call volume can be a grind - you'll hear "not interested" or get hung up on dozens of times per day. Small business owners are busy and often skeptical of salespeople.
• Campaigns are seasonal - Q4 is huge, January/February can be dead. Your pipeline needs to be 3-4x quota because not everything closes on time.
• Some internal bureaucracy - media plans need approvals, inventory can get tight for popular time slots, and you may have to navigate internal politics around splitting credit for deals.

What Success Looks Like

• Hitting $45K-$60K in booked revenue per month consistently
• Building a book of 30-40 active recurring clients who renew annually
• Booking 8-10 new first-time advertisers per month
• Converting 20-25% of your discovery meetings into closed deals within 60 days

Who You're Selling To

Primary Buyers:

• Small business owners (restaurants, auto dealers, retail stores, healthcare practices)
• Local marketing managers at regional chains
• Occasionally agency media buyers managing local client budgets

What They Care About:

• Reach and frequency - can you actually get in front of their target demographic?
• Cost per impression vs digital alternatives - am I overpaying for radio?
• Proof it works - case studies, attribution data, or testimonials from similar businesses
• Flexibility - can they pause or adjust campaigns mid-flight if results aren't showing?
• Bonus opportunities - event tie-ins, personality endorsements, on-air contests that create buzz

Requirements

• 2-4 years of B2B sales experience (media sales experience is a plus but not required)
• High tolerance for cold calling and rejection - you need to make 40+ dials per day without getting discouraged
• Strong communication skills for phone-based selling - you won't meet most prospects face-to-face
• Consultative selling ability - understanding client needs and building custom media solutions vs just selling spots
• Self-motivation to manage your own pipeline without much hand-holding
• CRM hygiene - logging calls, updating opportunities, forecasting accurately
• Must be in St. Petersburg, FL - this is an in-office role