From the boardroom to the finish line

From the boardroom to the finish line

I was an overweight lawyer watching an Ironman from the beach. A year later I raced one. Since 2015 I've coached 700+ athletes in 15+ countries to their own finish lines, plenty of them with calendars as full as yours.

Why athletes train with Wingman

I didn't come to this sport fit. I was a sports lawyer carrying extra weight and making poor choices about food, sleep and stress. I hired a coach for my first Ironman because I had no idea what I was doing, and that coach got me there. The energy I got back showed up at the office too.

Today our coaches work with every kind of athlete, from first-timers getting off the couch to age-groupers chasing a personal best. Plenty of them look like I did back then: somewhere between 40 and 60, running a business or a team, travelling more than they'd like, and short on time.

  • Your plan bends around your week

    A sick kid, a red-eye to London, a board meeting that runs three hours over. On Custom and One, your coach adjusts your plan daily so the week still counts.

  • Every session has a purpose

    We set your zones from real test data. Then we keep you out of the grey zone, where self-coached athletes spend most of their miles feeling tired and going nowhere.

  • Someone actually reads your data

    Wingman Black Box, our own software, pulls in everything from your watch, power meter, scale and sleep tracker. It turns that into a weekly report on compliance, fitness, fatigue, HRV and sleep, and that report shapes next week's training.

  • You don't train alone

    You get monthly squad calls, a WhatsApp group that's busy at 5am, and team races with Wingman coaches out on the course. We also coach the DC Tri Club's advanced programs. At Eagleman, 37 of our athletes lined up, all 37 finished, and 17 of them were racing it for the first time.

athletes
700+
countries
15+
Coaching online since
2015

Three Ways to Train with Wingman

Every tier runs on the same coaching philosophy that has taken 700+ finishers across 15+ countries.

Tier 01

Team Wingman

$195/month

+ $150 onboarding

Your plan, fitted to your week. Train with a cohort chasing the same finish line, with the full Wingman team behind you.

Setup

  • Welcome pack: cap, race belt, water bottle ($70 value)

  • Plan Fit Session at signup, plan mapped onto your actual week

  • Full setup: TrainingPeaks, devices, zones, insurance


Training

  • Proven Wingman plan via TrainingPeaks

  • TrainingPeaks Premium account included

  • Race cohort, training alongside your event

Coaching

  • Monthly team Zoom call with Stephan and the squad

  • Wingman WhatsApp community, group messaging

  • Race course preview and race-week support

  • Race support in person at official team races


The team

  • The Wingman Athlete Library: nutrition, race week, travel, data

  • Early access to the race calendar, race intel archive, finisher graphics

  • Team kit, store and monthly newsletter

  • Preferred pricing: Garmin, QR, TheFeed, Form, Rudy Project

  • Pause without penalty, plus race deferral at no charge

  • If you do not cross the finish line, I refund your coaching fees. The onboarding fee is not refundable.

  • Daily coach review of your training

  • Written performance reports

  • 1:1 coach contact or personalised plan

  • Swim and run video analysis

Most Popular

Tier 02

Wingman Custom

$345/month

+ $250 onboarding

Your race. Your plan. And a coach in your training every single day.

Everything in Team Wingman, plus

  • I review your training every day and comment on your workouts

  • Personalised plan built around your schedule, level and goal race

  • Training zone management, zones updated as your fitness changes

  • Test Week at the start to set zones from real data

  • Integrated strength training

  • TrainingPeaks Virtual cycling platform

Coaching

  • Performance report at least every two weeks

  • Monthly 1:1 call, plus more on demand whenever you need one

  • Direct 1:1 messaging in TrainingPeaks, 48hr reply

  • Monthly swim and run video analysis

  • Season planning and race selection call

Race Day

  • Personalised nutrition and hydration plan

  • Personalised race-day pacing plan

  • Post-race review with coach input

Extras

  • Real-time tracking, Garmin and wearable sync

  • Training camp discounts, waitlist priority on Wingman One

Tier 03

Wingman One

$549/month

+ $350 onboarding

My full attention. Fortnightly deep analysis, direct access, ten athletes only.

Everything in Custom, plus

  • A dedicated coach, yours exclusively


  • Onboarding call and full tech setup before you start

  • Full threshold testing, zones built from test data

Coaching

  • In-depth report at least every two weeks

  • Fortnightly 1:1 call, plus unlimited calls on demand

  • My direct WhatsApp, same-day reply in office hours

  • Unlimited swim and run video analysis

  • Ongoing custom nutrition coaching

Long Game

  • Quarterly performance review

  • Annual season roadmap

  • Race-day remote support, on-site at team races

Access

  • Limited to ten athletes at any one time

Our coaching packages cover your training, not your Ironman race ticket. You'll need to buy your race entry separately from the official race organiser.

How online coaching works

Coaching online since 2015, for athletes whose calendars are already full.

  1. We get to know you

    An onboarding call about your goals, history and schedule.

  2. We build your plan of attack

    A periodized plan built around your life, delivered to TrainingPeaks Premium.

  3. Your workouts come to you

    Sessions sync to your watch and guide you in real time.

  4. Your data comes to us, and Black Box goes to work

    Black Box turns every device's data into clear next steps.

Free tools from the Wingman playbook

These are the same calculators our athletes use every week. They're free, there's no sign-up, and each one takes about two minutes.

  • Hydration Planner

    Do a one-hour sweat test and get your race-day plan: how much to drink, how much sodium, and what to take at every aid station.

  • Tri Zones Calculator

    Get your bike, run and swim zones from three short tests, plus your 70.3 and Ironman race-day targets.

  • Marathon Zone Calculator

    Run one 30-minute test and get every heart rate zone and pace, adjusted for the heat.

Why choose us as your Wingman?

From Sprint to Full Triathlon | From Beginner Runner to Ultra Running | From Trail to MTB Cycling

Wingman Multisport coaches athletes worldwide for an impressive array of events from road running, open water swimming to road or mountain bike cycling. Based in South Africa and the United States of America, we specialize in triathlon coaching, including the Ironman 70.3 and Ironman distances. Our qualified triathlon coaches:

  • We've been in your shoes! Our coaches know what you are going through and have years of experience in getting you to the start line in the best shape ever. Our coaches can be Drill Sergeants, Hand holders or Cheerleaders, whatever method will work best for you.
  • Our coaches can restructure your workouts and training plans when you get sick, travel or having to deal with real life stresses like sick kids, work deadlines, etc.
  • Remove the guesswork. Let the experts navigate the technical stuff while you just focus on one workout at a time, saving you time and energy.

What will it mean for me?

  • Guidance and regular feedback to avoid “junk miles” and ineffective training which defies the purpose of working out
  • Keeps you accountable
  • A coach will help determine the correct types, intensity, frequency and duration of workouts that suits your lifestyle which, is super important in order to peak at the right time
  • You'll have a planned season with realistic, attainable goals
  • You are way more likely to reach your goals by leveraging the skills of a professional coach
  • A coach will ensure there is a healthy balance between getting fitter, fatigued, adapting and being fresh for your race

What our athletes say

Wingman Athlete Roger Polack

I can’t recommend Coach Stephan Weyers enough for triathlon training. If you’re considering any triathlon distance, hit up Stephan. I’m extremely grateful for his guidance and the great training plan he put together to help get me to the finish line in Ironman Wisconsin. As a bonus, he introduced me to Poolesville-area riding—what a gem in the DMV!

Thanks, Coach!

Roger Polack

Ironman Wisconsin finisher 2026

Wingman Athlete Werner Luus

I reached out to Stephan from Wingman Coaching because of his excellent reputation and mutual connections. In retrospect I realized that I lucked out big time having him as my coach.

Helping me from zero to Ironman 70.3 finisher in 9 months speaks for itself; behind the scenes was a plan and support that worked for me around the realities of a busy professional life.

I have no hesitation to recommend Stephan and team to anyone who wants to achieve their most ambitious goals.

Werner Luus

70.3 Weymouth finisher 2026 (2nd triathlon ever)

Wingman Athlete Rachel Bowers

Coach, you knocked it out of the park this weekend. I've never gone thru a program or had a coach outside of high school sports. Triathlon is HARD! It's awesome to have your guidance. Listening to me complain/panic in the water, gifting me the cadence meter, the camaraderie, advice on all things tri, the encouraging words on the sidewalk, your active participation, the countless high fives, LITERALLY pushing me up the hill, picking up NA Michelob Ultra for the finish and whatever else I'm missing.. you're the man. Grateful that you found triathlon & the desire to coach. I'm a better athlete because of you!!

Rachel Bowers

Ironman 70.3 Luxembourg finisher 2026

Wingman Athlete Bruce Weinelt

Triathlon is obviously an individual sport, but Vichy was a reminder how much better it can be when there is a real team around it. And a large part of that was down to our coach, Stephan Weyers, who created the atmosphere and sense of community that made the whole experience what it was — as coach, organizer, supporter and friend.

Bruce Weinelt

Multiple Ironman 70.3 finisher

Wingman Athlete Alex Aquilar

When I didn’t believe in myself, Coach Stephan was there, never letting me count myself out. More importantly, his coaching, mentorship, and support gave me the tools I needed to finish my first Ironman 70.3—even without doing the majority of the training. My journey wasn’t about natural talent or a flawless training cycle. It wasn’t about perfect preparation or impeccable execution. In the end, my journey to the finish line was about trusting in the belief that Coach Stephan had in me, and letting that belief carry me to the finish line. I chose, as Coach Stephan said to his athletes before the race, to be my best self in as many moments as possible, from the minute I hit the water through to the race down the red carpet to a near-miraculous finish. Thank you, Coach, for the unwavering support, for your incredible mentorship, and for never letting me give up.

Alex Aquilar

Ironman 70.3 finisher 2026

Wingman Athlete Jennifer Watson

After 25 years in triathlon, I know how much dedication this sport requires. I also know that as I get older, the challenges feel different and it becomes a mental game as much as a physical one. Last year, I experienced my first DNF, which shook my confidence. Working with Stephan made all the difference. He helped me rebuild that confidence, feel genuinely prepared, and ultimately return to finish an Ironman 70.3 one year later.

One of the things I appreciated most was his ability to adjust my training plan when I had an unexpected surgery that kept me out of the pool. Instead of losing momentum or fitness, he helped me adapt safely and stay on track. Stephan seems to know exactly when I needed a push, when I needed patience, and when I just needed someone to remind me that I was still an athlete.

I would highly recommend Stephan to any triathlete looking for a thoughtful, knowledgeable, and supportive coach—especially anyone navigating setbacks, shifting life priorities, or continuing to chase meaningful goals as you age.

Jennifer Watson

Multiple Ironman 70.3 finisher

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