SimplePractice raised Starter 69% in one step. Here's what that tells you about AI strategy.

The number that stopped me was not $49. It was the gap.

A therapist forwarded me her February 2025 SimplePractice notice and asked if this was normal. Starter had been $29 a month for years. The new floor was $49. Add the AI Note Taker at $35, and a solo clinician who wanted AI documentation went from $29 to $84. She had been paying the $29 for most of the time she had been in private practice.

That is a 69% list-price change on the base plan, plus a new $35 feature priced outside every plan. The reset officially landed on each account's billing date on or after March 3, 2025, so existing customers flipped between early March and early April, not all on day one (SimplePractice 2025 pricing live Q&A and subscription plan FAQ). Across roughly 14 months, February 2025 through April 2026, the line that matters to a practitioner who wants AI documentation (Starter plus Note Taker) moved 190%.

What follows is what I think that number is telling us, and when it matters enough to act on.

The 69% step is a pricing confession

A 69% move is the vendor admitting, out loud, that the prior price was wrong for the product they were shipping. Not slightly wrong. Wrong by a factor of roughly 1.7. Pricing teams have a name for this kind of move: reanchoring.

A 4–7% annual bump says the product improved a little and costs crept up. A move this large says the old price had come loose from the value the vendor now thinks it delivers, or from the margin target they are now running to. Either reading is defensible, and both matter for what comes next.

The part most therapists miss is that the new $49 is not anchored either. It is a number being tested against customer response, competitor positioning, and whatever internal margin targets the company is running. A price that moved this much once carries no structural resistance to moving again. In SaaS, a base-tier reset that lands cleanly tends to be followed by another adjustment 18 to 30 months later. Not inevitable. But not hypothetical either.

I talked last month with an LCSW in Austin — call her Priya — who runs a solo telehealth practice and signed up for SimplePractice Starter in early 2023. She was not planning to leave that day. Mostly she wanted to know whether she had missed a cheaper plan, or whether there was something on the pricing page she had read wrong. We spent the first ten minutes of the call checking the plan page together before she opened her spreadsheet. By summer of 2025, her SimplePractice invoice was larger than her malpractice premium. She is still on SimplePractice. She likes the measurement-based assessments and does not want to re-train her VA on a new system. She has also priced three alternatives since March without switching to any of them. That detail is probably the most representative thing in this whole article.

Why the Note Taker is a separate SKU

The detail most of the 2025 reprice commentary skipped: the AI Note Taker costs $35 per clinician per month regardless of which base tier you sit on. Starter ($49) plus Note Taker is $84. Essential ($79) plus Note Taker is $114. Plus ($99) plus Note Taker is $134. The AI price does not vary with the base plan (Note Taker FAQs).

The invoice tells the story. AI is not part of the plan. It is another charge on top of the plan.

That matters for how the vendor will move prices from here. When an add-on is priced identically across every tier, it can be adjusted independently of the base, and in practice vendors raise whichever number is easier to justify in a given quarter. A practice planning three years out is now watching two numbers instead of one.

What the review boards are saying

I would not build a churn model from PissedConsumer and BBB pages. But I would read them before signing anything for three years. The pattern worth noticing is simple: after the March 2025 reprice, public complaints about billing and cancellation friction are easy to find. The PissedConsumer board sits at a 1.8-star average, and the BBB profile shows the same themes repeated across reviewers.

The vendor's internal numbers are not available for a sanity check. Vista Equity took EngageSmart private in January 2024, so the quarterly filings that used to exist simply do not anymore. What is left is review-board signal, what customers report in practitioner forums, and what individual practices say on calls like the one with Priya. None of that is proof. All of it is worth reading before locking in a multi-year decision.

Three-year cost — 1, 3, and 5 therapists

I picked 1, 3, and 5 therapists because those are the points where the decision changes shape. Solo is a personal expense; you move platforms if you feel like it and keep them if you are happy. Three clinicians is a payroll conversation, the first time software costs show up in the same meeting as salaries. Five clinicians is the size where a monthly software line can quietly cost the practice a full hiring slot over three years.

The math below uses SimplePractice's Plus plan plus the $35 Note Taker against Oli Health's flat $20 per clinician. SimplePractice Plus charges $99 for the primary clinician and $74 for each additional clinician in a 2–5 clinician group, per the Group practice FAQ. Starter and Essential do not support group practices, so any multi-clinician mental health practice defaults to Plus. All SimplePractice figures are list price per simplepractice.com/pricing, accessed April 2026.

A few things the table is not doing. It uses list pricing (SimplePractice advertises a 50%-off-for-3-months promo and a referral credit; Oli has seasonal credits but nothing structural), so a real invoice may look 5–15% different in the first year. It also assumes the practice runs Plus. SimplePractice Plus includes mental-health-specific tooling such as auto-administered PHQ-9 and GAD-7 and treatment plans tied to CPT codes, which Oli does not yet match at parity. Three years is the budget horizon most practice owners plan against, which is why small monthly deltas compound into real money. A 5-therapist practice staring at $20,520 on one side and $3,600 on the other has a $16,920 line item that belongs in a board meeting.

For a broader look at how these numbers compare against other mental-health and allied-health platforms, see practice management software pricing compared.

What SimplePractice still does better

SimplePractice has real depth in mental-health-specific workflow. The measurement-based care tooling, which covers auto-administered PHQ-9, GAD-7, and outcome tracking across sessions, is mature in a way that takes years to build. Treatment plan templates tie into CPT codes and the insurance billing path in ways that matter when a claim gets denied and a clinician has to argue it back. A practice whose daily workflow runs through those features should think hard before switching, and probably stay put if the honest answer to "do I use these every week" is yes.

Oli's measurement-based care is catching up rather than leading. Outcome tracking is there; the auto-administered assessment library is narrower, and the insurance billing workflow is newer. If that is load-bearing for how a practice sees patients, the April 2026 comparison is not a tie yet. Worth revisiting in six months. The gap is closing but it is not closed.

What this looks like on Oli, briefly

Oli Health is $20 per clinician per month, flat. USD in the US, CAD in Canada. AI documentation, AI intake, scheduling, payments, and notes ship inside the plan. There is no separate Note Taker charge because the AI is not a separate SKU.

That is a commercial choice on our side with a clear trade-off. We make less per seat than SimplePractice does after the 2025 reset. The bet is that the all-in price wins the three-year decision, especially once a practice moves past one therapist. The table above is what that bet looks like spelled out.

For the retention side of the same question, the real cost of not switching an EMR unpacks what changes when a practice waits a hike out instead of acting on it.

I would not leave SimplePractice just because the invoice got bigger. I would leave if the parts of SimplePractice I use every week are scheduling, notes, billing, and AI documentation, because at that point the comparison stops being philosophical and becomes the bill. If a practice lives inside the measurement-based care tooling or the insurance billing quirks SimplePractice has solved over a decade, the bill is a line item to absorb and the 2025 reprice is an annoyance rather than a decision. If it does not, the arithmetic in the opening is where the conversation starts.

For the longer argument about how pre-AI and AI-native platforms price AI differently, traditional vs AI-first practice management goes deeper on the architectural reason one invoice has a Note Taker line and the other does not.

Quick reference