Brand Partner

Walk-On Holdings owns and operates a network of daily finance newsletters reaching roughly 300,000 subscribers combined, delivered across three points in the day: pre-market, midday, and after-close/weekend.

We monetize through sponsorships priced on a straightforward, performance-based model with a guaranteed minimum outcome built into every deal. No CPM guesswork, no opaque bundles, which makes this a genuinely easy story to sell once you're in front of the right person.

The Role

We're looking for someone who wants to play a real role in growing a fast-moving media business. You'll serve as an evangelist for Walk-On Holdings externally — clearly articulating our value proposition to prospective sponsors, agencies, and partners — while working closely with an AI-powered system that handles the heaviest lifting of prospecting.

That system spots companies already spending money on newsletter advertising, researches other companies that could be a great fit even if they've never sponsored a newsletter before, identifies the right person to contact, finds their email and LinkedIn, and drafts personalized outreach messages.

Your job starts where the AI's output lands on your desk.

You're the human in the loop: you point the AI at new sponsor categories and agency relationships worth exploring, you check its work, you're the one who actually sends the outreach, you own the relentless follow-through that most people give up on too early, you keep the whole pipeline organized, and you get interested prospects booked onto the calendar.

This is a persistence-and-judgment role more than a research role. The research is done for you, but making sure nothing falls through the cracks is on you.

Responsibilities at a Glance

• Serve as an evangelist for Walk-On Holdings externally, clearly articulating our value proposition to sponsors and agency partners
• Direct our AI system toward promising new sponsor categories and source/maintain relationships with media and creative agencies, with a sharp focus on financial brands
• Review every AI-generated prospect package for accuracy before anything goes out under your name
• Send outreach personally and follow up persistently until you get an answer
• Multi-thread accounts — find and approach a new contact when the first one goes quiet
• Stay current on the newsletter and digital media industry, and on what competitors are doing, to keep spotting new opportunities
• Keep the pipeline dashboard current and accurate at all times
• Get interested prospects booked onto the calendar with good context passed along
• Represent Walk-On Holdings professionally in any partner or industry-facing conversations
• Meet and exceed targets for qualified meetings booked and pipeline generated, with revenue targets added once the role expands into closing

Step-by-Step: What You'll Actually Do

1. Direct the AI to find new sponsor categories and agency relationships

Beyond companies we spot sponsoring other newsletters, you'll use AI to proactively source prospects who aren't advertising in newsletters yet but would be a strong fit for our audience — think public companies, alternative asset managers, accounting firms, estate planning companies, and ecommerce brands selling products or services our readers would care about. This also includes media and creative agencies that place ads on behalf of multiple brand clients — landing one agency relationship can open the door to several sponsors at once. You bring the ideas and judgment on what's worth exploring; the AI does the legwork of researching and building out the prospect list.

2. Review the AI-generated prospect package

For every sponsor prospect, the AI delivers a complete package: the company and placement details (if applicable), a proposed point of contact (with title and reasoning), their email (flagged as verified or best-guess) and LinkedIn profile, a personalization hook, and drafted messages (email, LinkedIn connection note, LinkedIn InMail).

Your job here is quality control: does the contact look right for this company's size and structure? Does the email look plausible? Does the draft actually make sense and sound right? Catch anything off before it goes out — you're the last check before this reaches a real person.

3. Send the outreach

Once you've confirmed the package looks right, you send it yourself — the email from your inbox, the LinkedIn connection request and/or InMail from your account. This is not automated; it's you sending a message you've personally reviewed and stand behind.

4. Follow up... at least 5 times

Most deals are lost to giving up too early, not to a "no." For every prospect who doesn't respond, follow up a minimum of 5 times across email and LinkedIn before moving on. Space these out sensibly (not all in one week), vary the angle each time, and keep it persistent but professional.

5. Multi-thread the organization

If the original contact goes quiet after your follow-up sequence, don't just drop the account. Go back to the AI-identified backup contact (or ask for one) and start a fresh thread with someone else at the same company — a different title, a different angle. Many deals move forward through the second or third person, not the first.

6. Stay sharp on the industry

Keep up with what's happening in the newsletter and digital media space: new players, competitor sponsorship activity, industry events worth attending, and trends in how financial brands are spending on media. This isn't a one-time task; it's ongoing awareness that feeds back into which sponsor categories are worth pursuing next.

7. Keep the pipeline organized

Track every prospect's status as it moves: outreach sent → follow-ups in progress → replied → meeting booked. The AI helps you keep this current and can flag prospects that have gone quiet and are due for a follow-up or a new contact, but you're responsible for making sure nothing falls through the cracks.

8. Book the call

Once a prospect replies or shows real interest, your job is to get them booked onto a call directly on the founder's calendar. Confirm availability, schedule cleanly, and pass along good context. Who the prospect is, what caught their interest, anything relevant from the email/LinkedIn thread, so the call starts strong. The founder will run the call from there.

What Success Looks Like

• Every AI-generated prospect package gets a careful, honest review before anything goes out under your name
• A steady flow of new, well-chosen sponsor categories and agency relationships added to the pipeline, not just companies we happen to spot elsewhere
• Outreach actually goes out, on time, in your voice
• No prospect gets fewer than 5 real follow-up attempts before you move on
• When the first contact doesn't work out, you find and try the next person rather than giving up on the account
• A pipeline that's always current, so nothing goes stale or gets forgotten
• Calls booked cleanly and consistently, with good context handed off
• Growing knowledge of the newsletter/digital media landscape that translates into sharper prospect ideas over time

Who You Are

• Highly organized and disciplined about follow-up, you don't let things slip, and you don't give up after one unanswered email
• Curious and commercially minded, you can look at our audience and generate real ideas for who else might want to reach them, beyond the obvious
• Comfortable building relationships with agency contacts as well as brand-direct contacts
• Good judgment. Comfortable reviewing AI-generated work critically rather than sending it blindly
• Clear, professional communicator, comfortable adapting a drafted message in your own voice when needed
• Resourceful. If the first contact at a company doesn't respond, you know how to find and approach the next one
• Genuinely interested in the digital media/newsletter industry and motivated to keep learning it
• Bonus: experience with outbound sales, SDR/BDR work, or account management where persistence and multi-threading were part of the job

Tools You'll Use

• An AI-powered prospecting system that researches companies, finds contacts, and drafts your outreach
• A pipeline-tracking dashboard (already built) with KPIs, pipeline stage view, and per-prospect detail including drafted messages ready to send
• Your own email and LinkedIn account for sending outreach and follow-ups
• Calendar booking tools for scheduling calls

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