Headway vs Owl Practice
Headway scores 7.2/10 vs 7.0/10. Best for: Solo therapists who want zero startup costs and fast insurance credentialing.
Headway scores higher overall at 7.2/10 vs 7.0/10. 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.
Headway 
Owl Practice Rank
#20 of 41
Rank
#28 of 41
Features
12/18
Features
15/18
Starting at
$0/mo
Starting at
$25/mo
User reviews
—
User reviews
4/5 (72)
What they cost
| Headway | Owl Practice | |
|---|---|---|
| Starting at | Free /mo | $25 /mo |
| Free trial | Free tier available | 14 days |
| Number of plans | 1 | 4 |
What the pricing really means
At first glance, Headway looks cheaper at $0/month vs $25/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 Owl Practice wins
- Built specifically for Canadian mental health professionals. PIPEDA/PHIPA compliance, Canadian billing codes, and provincial insurance requirements are all native, not bolted on
- Measurement-based care tools on the Pro plan let you track client outcomes with standardized assessments, which most competitors charge extra for or skip entirely
- Admin staff accounts are free. You only pay per clinician who sees clients, which saves real money in a group practice
- APA-endorsed, which gives it credibility if you are a psychologist looking for something vetted by your professional association
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 Owl Practice falls short
- Small review count (72 on Capterra). The user community is much smaller than SimplePractice or TherapyNotes, so you will find fewer tutorials and forum answers
- No mobile app. Managing your schedule between sessions means logging into a browser
- Insurance claims cost $0.25 each and eligibility checks $0.15 each on top of your monthly fee. Those per-transaction costs add up if you file 100+ claims a month
- The introductory pricing ($25/month for Starter) jumps significantly after the promo period, so check the regular rates before committing
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.
Owl Practice
Target: 1-10 clinicians
Buy Owl Practice if you are a Canadian therapist or psychologist who needs PIPEDA compliance and Canadian billing built in from day one. Skip it if you are US-based or want a large user community with plenty of third-party resources.
Feature comparison
| Feature | Headway | Owl Practice |
|---|---|---|
| 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
Headway scores 7.2/10 vs Owl Practice's 7.0/10 in our ranking. Headway is the better pick for 1 provider. Owl Practice is better if you need canadian psychologists and therapists who want an ehr built for their regulatory and billing requirements without paying us-centric software prices.
Headway starts at $0/month. Owl Practice starts at $25/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. Owl Practice: Yes, 14-day free trial. Always test with your actual workflow before committing to an annual plan.
Headway covers 12 of 18 features we track. Owl Practice covers 15 of 18. Owl Practice 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. Owl Practice does not.
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 Owl Practice if...
Canadian psychologists and therapists who want an EHR built for their regulatory and billing requirements without paying US-centric software prices