Head of Loyalty

Head of Loyalty

TrueLoyal · San Antonio, United States · — · Posted 2026-09-12

Workplace: on_site

Description

Location: San Antonio, TX

Reports to: CEO

Department: Executive Leadership

Team: None at the start

Travel: Occasional — conference speaking, pre-sales and post-sales work

About TrueLoyal

TrueLoyal is the loyalty engine powering today’s fastest-growing consumer brands to help them build customers for life. We combine AI-driven personalization with a proven growth strategy to help brands nurture customers everywhere they sell—eCommerce, retail, and distributor channels. Capturing every in-store swipe and online transaction, TrueLoyal tailors every customer interaction, turning transactions into relationships and relationships into repeat revenue.

The Role

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.

Here is why the role exists. A buyer told one of our reps he was on his third loyalty vendor call that day. Another said most of the options in the market look the same to him. They are both right about the software—points, tiers, referrals, receipt scanning. Everybody has a version of it, and the demos blur together by the third one.

What those buyers cannot get on the other two calls is somebody who has actually built one of these. Who knows what the earn rate should be, what the liability looks like in year three, and which half of the plan in front of them will not survive contact with their finance team. We already sell that—program design, program economics, competitor benchmarking, and an honest read on whether the thing will work. It is the reason buyers pick us over the other two calls. Nobody owns it. That is this job.

You will not get a big team. You will get a corpus of recorded customer calls, live loyalty program data across 300+ consumer brands, a strategy practice that needs a standard, an AI that needs teaching, data and AI teams to build it with, and a company that will move if you are right.

Who We Sell To

Mid-market consumer brands doing $50M to $500M, selling through Walmart, Target and Amazon on one side and their own site on the other. North America first, with CPG reaching into the UK and Western Europe. The buyer is VP or Director level—brand managers, ecommerce managers, retention managers, CMOs.

Note what that means for the work: our customers largely do not own their own point of sale. Identity is fragmented, purchase data arrives second-hand, and receipt scanning does a job that a swipe does elsewhere. If you have built a program for a brand shaped like this, you already know what they will ask for and what they will get wrong.

Key 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.

Scope, Plainly

You own who we sell to and why they buy; the loyalty program designs and strategy work that reaches a client, and the standard it is held to; the demand case for what we build next, worked through with our VP of Product; what our AI knows about loyalty program design, and the judgment it learns from; and our public voice on loyalty, on stage and in the room.

You do not own a quota or a department. Our Program Operations team runs client programs day to day. The product backlog and release calls sit with our VP of Product, but you help shape the roadmap together.

Requirements

What We’re Looking For

Start here: you have to know loyalty. Not as the leading authority alive, but as somebody who has built a program, run one, or sat close enough to one to know how they get priced, why members go quiet, and what a points liability line does to a CFO’s mood. Most of the rest of this list is learnable on the job. The loyalty part is not.

• 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.

Not a Fit If

• 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.

First 90 Days

• Day 30—you have been through the call corpus and told us three things we are wrong about, and one thing we should build.
• Day 60—you have published the loyalty program design standard and put a plan through it that we could hand a client tomorrow.
• Day 90—our AI drafts that same work at a quality you would sign, and your time goes to the exceptions.

Why Join TrueLoyal

• Own the thing that makes us different. The loyalty depth is already why buyers pick us over the other two calls on their calendar—nobody owns it yet, and you would.
• A direct line to the CEO, and an influential seat where your read on the market changes what we build and who we chase.
• A rare data position: live loyalty program data across 300+ consumer brands plus a recorded call corpus, with nobody currently sitting with all of it.
• Build the AI layer on top of your own judgment, and ship it as product.
• Join a team that values collaboration, adaptability, speed, and results over politics and red tape.
• Competitive compensation package

Benefits

• Health insurance plan with $0 deductible and $0 co-pay.
• Dental and vision insurance plans.
• Flexible spending account option.
• Open PTO Policy plus 9 paid holidays per year.
• Participation in our 401(k) savings plan
• Company-paid Life and AD&D coverage

Apply

Apply at TrueLoyal

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