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The Training Business Newsletter

👋 Welcome to TryTami's weekly newsletter, where we break down what’s happening in the training industry and what training leaders need to know in 2026.

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TL;DR: Over the last few months I've been on a lot of calls with training company CEOs and L&D leaders running serious instructor-led programs. The same five operational problems keep surfacing no matter who's on the other end of the line, whether it's a boutique training shop doing $2M a year or an enterprise L&D team running thousands of sessions. Below are the top 5 challenges training leaders are facing and how to solve them.

1. "We're being asked to do more with fewer people"

This is the line I hear first on almost every call. Training demand is climbing. Headcount is flat or shrinking. The CEO is being asked to absorb more programs, more clients, and more reporting without growing the back office.

What I've watched happen: every new client adds a spreadsheet, a calendar invite, and eventually a hire. Coordination scales linearly with volume because the work behind every session is still being done by a person. Most ops teams I see have one or two coordinators, and the only knob the CEO has left when the business grows is hiring another one. Margin disappears into overhead instead of falling to the bottom line.

The leaders who break out of this don't hire their way through it. They automate the coordination work, things like instructor matching, reschedule notifications, and self-service registration, then pull two to three times the session volume through the team they already have.

My takeaway: if your only lever for growth is hiring another coordinator, the operations platform underneath isn't doing its job.

2. "Our operations lives in a million spreadsheets, inboxes, and calendars"

Almost every training company I talk to runs on the same stack: a million spreadsheets, a shared calendar, a CRM, an LMS, an email thread, and a billing tool. Bookings live in one place, the schedule in another, proposals in a PDF, invoices in Stripe. Some of it lives in peoples heads or tribal knowledge.

The cost adds up faster than CEOs expect. The licenses are cheap. The labor between them is not. A reschedule fans out into fourteen emails. A new client onboarding takes a week because no two records live in the same system. Just the tool sprawl plus the integration work to keep it standing tends to run $35K to $45K a year before you count the time spent stitching it together.

My takeaway: if your operations stack has more than two tools in it, you have a workflow held together by your team's memory, not an actual system. Eight tools belong inside one platform purpose-built for training.

3. "Our LMS wasn't built for instructor-led training"

Almost every training leader bought a learning management system years ago to deliver self-paced content. Now the business has shifted toward ILT and VILT, and they're trying to run instructor-led operations on top of a tool that was never designed for it.

An LMS is built for the learner: completions, certifications, content consumption. Most LMS platforms do that job well. A training management system (TMS) is a different category, built for the business of training:

  • scheduling classes at scale

  • instructor matching based on availability

  • student registration and evaluation

  • billing and payments

  • dashboards and reporting

A TMS like TryTami treats courses, instructors, clients, and revenue as first-class objects instead of afterthoughts to a learner experience.

What I see when teams force an LMS to do TMS work: a third-party scheduling tool taped on, manual instructor rosters, billing workarounds, and a registration page that doesn't talk to the CRM. The patchwork holds until a reporting question comes up that needs four systems to agree on what "completed" means.

My takeaway: most training operations need both. The LMS is what learners use. The TMS is what runs the business. Forcing one to do the other's job is where the workarounds start.

4. "I have no visibility into what other teams or locations are doing"

This conversation surprises me every time it comes up, and it comes up a lot, especially with multi-region training providers and enterprise L&D teams. The CEO or VP of L&D can't see across their own organization. Each region, business unit, or training center is running its own spreadsheet, its own calendar, and its own revenue tracker.

The cost shows up in three places. Capacity in one region stays invisible to another, so you turn down work while a trainer two states over sits idle. Cross-sell dies because no one sees the full picture of what a client buys across the network. And month-end becomes a consolidation exercise rather than a close. None of this is a line item, but all of it shows up in the margin.

The fix isn't forced centralization. The leaders solving this well preserve regional autonomy and add one source of truth on top: shared visibility into capacity, revenue, and utilization without forcing every region into the same inbox.

My takeaway: the silo tax is real money. If you can't see across your own training operation, neither can your buyers.

5. "I don't know my real numbers until month-end"

This is the one that bothers me the most because it's the one that's most fixable. Almost every training operations leader I talk to admits they can't answer basic questions in real time.

Which courses are actually profitable after instructor cost and admin time? Which instructors are over-utilized and which are idle? Which clients are scheduling less than they used to, before the renewal conversation? What does the next ninety days of revenue look like based on the actual schedule?

The data exists. It's just sitting in five different tools that don't talk to each other, and the only person who can stitch it together is finance, once a month, after close. By the time the problem is visible, it's already cost you the quarter.

The category for solving this is called ops intelligence: a layer that surfaces profitability, utilization, and risk live (not at month-end) and raises the most critical issues to the operators who can act on it. Course profitability per session, instructor utilization curves, client health signals, and a ninety-day revenue forecast based on the schedule. Visible in the same place you run the operation.

My takeaway: training operations should know what's working (or not) before the books do. If your dashboard is a finance export, you're operating thirty days behind reality.

How We’re Solving The Biggest Training Challenges

Every problem above has the same shape. A workflow that should be one action gets stretched into fifteen because the operations platform underneath isn't built for the way training actually runs.

The fix isn't more headcount, more tools, or another integration. It's one operations platform built for instructor-led training, where courses, instructors, clients, and revenue all live as first-class objects in a single system.

This is what we’re building at TryTami. If any of the five challenges above sound familiar, I'd be glad to walk you through how training businesses are solving them on the platform.

Thanks for reading,
Dave

About the author: Dave Murphy is co-founder of TryTami, the operations platform purpose-built for instructor-led training providers and corporate L&D teams. He works directly with training company CEOs, ops leaders, and L&D heads on scaling ILT operations without growing the back office.

Frequently Asked Questions

What are the biggest challenges in training operations?

The five biggest operational challenges training companies face in 2026 are doing more with fewer people, running operations across spreadsheets and email instead of one platform, forcing an LMS to do the job of a training management system, lacking visibility across teams or regions, and not knowing real numbers until month-end close. Each one quietly compounds margin loss across every program delivered.

Why doesn't an LMS work for instructor-led training?

An LMS is built for the learner: completions, certifications, and self-paced content consumption. Instructor-led training is a different operational job that requires scheduling, instructor matching, registration, billing, and reporting. Most LMS platforms treat ILT as an afterthought, forcing teams to bolt on third-party schedulers, manual instructor rosters, and billing workarounds. A training management system (TMS) is the category purpose-built for ILT operations.

How do training companies scale without adding headcount?

Training companies scale without adding headcount by automating the coordination work that grows linearly with session volume: instructor matching, reschedule notifications, self-service registration, and reporting. The operators who break through replace eight-tool stacks (spreadsheet, calendar, CRM, LMS, email, billing) with one operations platform built for instructor-led training, and run two to three times the session volume on the team they already have.

What's the difference between a TMS and an LMS?

A learning management system (LMS) delivers content to learners through courses, completions, and certifications. A training management system (TMS) runs the business of training through scheduling, instructor matching, registration, billing, and reporting. The LMS is what learners use; the TMS is what runs the operation. Most training providers need both: an LMS for the learner experience and a TMS for the operations layer underneath.

How do you measure training operations performance?

The five core metrics that define training operations performance are course profitability (revenue per session after instructor cost and admin overhead), instructor utilization (booked hours versus available hours), client health (booking frequency, evaluation scores, on-time payment), pipeline velocity (time from proposal to scheduled session), and forward-revenue visibility (a ninety-day forecast based on the actual schedule). The most operationally mature training companies surface all five live, not at month-end close.

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