Headway vs SimplePractice
SimplePractice scores 7.8/10 vs 7.2/10. Best for: Solo therapists or small group practices that want one platform for scheduling, notes, telehealth, and billing without stitching together multiple tools.
SimplePractice scores higher overall at 7.8/10 vs 7.2/10. Buy SimplePractice if you want the most widely-used platform with solid telehealth and a genuine mobile app that works between sessions. Skip if you care about customer support speed or need advanced insurance billing without per-claim fees.
Headway 
SimplePractice Rank
#20 of 41
Rank
#10 of 41
Features
12/18
Features
18/18
Starting at
$0/mo
Starting at
$49/mo
User reviews
—
User reviews
3.9/5 (2943)
What they cost
| Headway | SimplePractice | |
|---|---|---|
| Starting at | Free /mo | $49 /mo |
| Free trial | Free tier available | 30 days |
| Number of plans | 1 | 3 |
What the pricing really means
At first glance, Headway looks cheaper at $0/month vs $49/month. But sticker price is only part of the story. Look at what is included on the base plan, how many users you get, and whether you need add-ons to get the features you actually need. The $99/month plan that requires $200 in add-ons is actually more expensive than the $250/month plan that includes everything.
Where Headway wins
- Completely free for providers — zero monthly cost
- Insurance credentialing done in weeks instead of the usual months
- 65,000+ providers across all 50 states
- AI-assisted session notes via built-in Scribe
Where SimplePractice wins
- 30-day free trial with no credit card required, so you can actually test it with real clients before paying
- Telehealth included on all plans, even the $49/mo Starter, which most competitors charge extra for
- Mobile app handles progress notes, scheduling, and telehealth between sessions without needing a laptop
- 225,000+ practitioners use it, which means community forums, YouTube walkthroughs, and third-party templates are everywhere
Where Headway falls short
- Headway owns your credentialing — if you leave, you may need to re-credential
- Commission from insurance reimbursements means you earn less per session
- No e-prescribing
- Not built for group practices — every provider must be individually licensed and credentialed
Where SimplePractice falls short
- G2 rating dropped to 3.9/5, which is low for the market leader and points to real frustration among power users
- No e-prescribing without a DrFirst add-on, so psychiatrists and prescribers will need another tool
- Support response times have slipped according to recent reviews, with some users waiting days for non-urgent tickets
- API access is locked behind the Plus plan at $99/mo, so automating workflows on the cheaper plans is not possible
Who is each product built for?
Headway
Target: 1 provider
Buy Headway if you're a new solo therapist who wants zero startup costs and fast insurance credentialing. Skip if you want full control over your insurance panels or run a group practice.
SimplePractice
Target: 1-10 clinicians
Buy SimplePractice if you want the most widely-used platform with solid telehealth and a genuine mobile app that works between sessions. Skip if you care about customer support speed or need advanced insurance billing without per-claim fees.
Feature comparison
| Feature | Headway | SimplePractice |
|---|---|---|
| Compliance & Security | ||
| HIPAA compliant | ||
| Telehealth / video sessions | ||
| Secure messaging | ||
| Scheduling & Clients | ||
| Online scheduling | ||
| Client portal | ||
| Intake forms / assessments | ||
| Automated reminders | ||
| Clinical | ||
| Progress notes / documentation | ||
| Treatment plans | ||
| E-prescribing | ||
| Outcome measures / assessments | ||
| Billing & Payments | ||
| Insurance billing / claims | ||
| Payment processing | ||
| Superbill generation | ||
| Automated billing | ||
| Platform | ||
| Group practice support | ||
| Mobile app | ||
| Integrations / API | ||
Common questions
SimplePractice scores 7.8/10 vs Headway's 7.2/10 in our ranking. SimplePractice is the better pick for 1-10 clinicians. Headway is better if you need solo therapists who want zero startup costs and fast insurance credentialing.
Headway starts at $0/month. SimplePractice starts at $49/month. Watch for add-on costs — the base price often does not include all features. Pricing last verified 2026-04-01.
Headway: Free tier available. SimplePractice: Yes, 30-day free trial. Always test with your actual workflow before committing to an annual plan.
Headway covers 12 of 18 features we track. SimplePractice covers 18 of 18. SimplePractice has broader feature coverage, but more features does not always mean better — pick the tool that covers what your business actually needs.
Yes, Headway has a mobile app. SimplePractice does too.
Yes. The main effort is migrating your data (customer lists, job history, invoices). Plan for 1-2 weeks of overlap where you run both. Most healthcare practice management tools can import CSV data. Ask both vendors about migration support before you sign.
The bottom line
Pick Headway if...
Solo therapists who want zero startup costs and fast insurance credentialing
Pick SimplePractice if...
Solo therapists or small group practices that want one platform for scheduling, notes, telehealth, and billing without stitching together multiple tools.