Head of Loyalty

TrueLoyal•San Antonio, TX

11d•Hybrid

About The Position

We’re hiring a Head of Loyalty to be the loyalty depth in a loyalty software company. Roughly seventy percent of the job is inside the business doing the work. Thirty percent is in front of the market, a reason people call us. This role exists because buyers often find loyalty software options to be similar, lacking someone with practical experience in building and managing loyalty programs. The Head of Loyalty will be responsible for program design, program economics, competitor benchmarking, and providing an honest assessment of program viability. While not managing a large team, this role will have access to recorded customer calls, live loyalty program data from over 300 consumer brands, a strategy practice, an AI that needs development, and data/AI teams to collaborate with. The company is looking for someone who can establish standards for loyalty work, develop an AI that can assist in this, and represent the company in the market.

Requirements

Real loyalty domain knowledge—a program you built, ran, launched, relaunched, or owned a meaningful piece of. You know why programs go quiet by year three.
You have worked the mechanics: earn rates, tiers, redemption behavior, breakage, and the economics that decide whether a program survives its own success.
You understand the finance side —liability, accrual, and the number that makes a CFO stop the meeting.
You have watched a program go flat and you know what caused it. That scar is worth more here than a clean record.
Brand or category experience in consumer goods or retail - you know enough about how a brand team thinks and what makes them ignore a recommendation.
Ideally, experience with programs where the brand does not control the point of sale—third-party retail plus DTC, receipt-based or inferred purchase data rather than a clean transaction stream.
You write well and fast, and you would rather produce the thing than brief somebody else to produce it.
You already use AI tools to do more work than one person should be able to do, and you want to push that a lot further.
You are good on a stage and better in a room.

Nice To Haves

Your loyalty knowledge only comes from reading about it. This is the one thing we cannot teach you here.
You want to direct the work rather than produce it.
You produce beautiful research nobody acts on.

Responsibilities

Program design and economics (30%)—own program economics as the standard everything else is measured against: earn and burn structures, tier design, breakage assumptions, redemption behavior, and the pricing that decides whether a program survives its own success.
Build loyalty program designs and run account reviews of live programs with a real recommendation attached, not a deck.
Model the liability and accrual picture behind every design, so that when we put a number in front of a brand it holds up in front of their CFO.
Produce at a volume one person could not hit alone, using AI and every tool we can buy to get there, and own the bar that all loyalty work clears before it leaves the building—both the recommendation that wins the deal and the program we build after they sign.
The loyalty market (20%)—know the loyalty market better than anyone here. Sit with the call corpus and the live program data across 300+ brands and say what it adds up to: what is working in the category, what has stopped working, and what the good programs are doing that ours are not.
Translate what you find into a demand case for what we build next—what our ICP keeps asking for that we cannot do yet, what buyers stitch together across three tools because we only cover one—and work the roadmap with our VP of Product with the evidence attached.
Shape the next call on where we sell. Watch the bets we place, and tell us early when one is working and faster when it is not.
Teaching the AI (20%)—teach our AI to produce the work above without you in the loop: first drafts of program designs, account reviews, feature explanations, content in our voice. Correct it when it is wrong and keep doing that until the output holds up in front of a client.
Work with our data and AI teams to make AI loyalty program design something we ship rather than something we only run in house.
Out in front (30%)—be the reason people call us. The loyalty conferences, the panels, the podcasts and the analyst conversations. We want our name on the short list when someone starts reading about this.
Sit in the pre-sales calls where a buyer wants to talk to someone who has actually done this, and in the post-sales rooms where a program is not landing and the client needs somebody senior with them.
Write, and write things people argue with.