Dialpad vs Five9
Thesis: Overlapping use cases, different tradeoffs — Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Comparison thesis: Overlapping use cases, different tradeoffs. Choose Dialpad only if your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape. Choose Five9 only if your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape. Workflow advantage: Dialpad leans business-phone, team-communication; Five9 leans contact-center, customer-messaging. Trade-off: you gain focus on one product's motion at the cost of the other's adjacent coverage — no universal winner. Major differences: - Buyer thesis: Overlapping use cases, different tradeoffs — Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. - Positioning: Dialpad is AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard from $15/user/month annual; Sell and Support are sep; Five9 is Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/Enterprise quote — 50-seat minimum.. - Company-size focus: Dialpad (small-business, mid-market, enterprise) vs Five9 (mid-market, enterprise). - Workflow coverage skew: Dialpad-leaning business-phone, team-communication vs Five9-leaning contact-center, customer-messaging. - Researched limits: Dialpad — Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price; Five9 — 50 concurrent-seat minimum — not viable for small SMB phone buyers. Limitations — Dialpad: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price; Connect Pro has a 3-user minimum; Enterprise requires 100 users; Five9: 50 concurrent-seat minimum — not viable for small SMB phone buyers; Digital is non-voice; Core is the published voice+digital entry. Poor-fit cases: Dialpad is a poor fit when that limitation bites: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price · Five9 is a poor fit when that limitation bites: 50 concurrent-seat minimum — not viable for small SMB phone buyers · Avoid Dialpad if you actually need Five9's motion (Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; ) Neither product has a completed hands-on product test on SoftwareGlimpse — this comparison is research/data-based only.
Dialpad
AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard from $15/user/month annual; Sell and Support are separate product ladders.
Best for
- • your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
- • use-case priority is business-phone and Five9 is secondary for that motion
Starting from $15.00/user/mo
No free plan
VS
Our verdict
Comparison thesis: Overlapping use cases, different tradeoffs. Choose Dialpad only if your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape. Choose Five9 only if your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape. Workflow advantage: Dialpad leans business-phone, team-communication; Five9 leans contact-center, customer-messaging. Trade-off: you gain focus on one product's motion at the cost of the other's adjacent coverage — no universal winner. Dialpad is a poor fit when that limitation bites: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price Five9 is a poor fit when that limitation bites: 50 concurrent-seat minimum — not viable for small SMB phone buyers Hard limitation for Dialpad when it matters: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price. Hard limitation for Five9 when it matters: 50 concurrent-seat minimum — not viable for small SMB phone buyers. Neither product has a completed hands-on product test on SoftwareGlimpse — this comparison is research/data-based only. Pricing threshold: estimate spend with the cost calculator before shortlisting.
Dialpad is better for
- ✓ Analytics
- ✓ AI features
Five9 is better for
- ✓ Power dialer
- ✓ CRM / CTI integrations
Tie
- • Number / country coverage
- • WhatsApp Business
- • Routing & IVR
Choose Dialpad if: your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
Choose Five9 if: your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
Five9
Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/Enterprise quote — 50-seat minimum.
Best for
- • your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
- • use-case priority is contact-center and Dialpad is secondary for that motion
Starting from $119.00/user/mo
No free plan
Quick verdict
Start here — then dig into the evidence below.
Choose Dialpad if…
- your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
- use-case priority is business-phone and Five9 is secondary for that motion
- You prioritize analytics
- You prioritize ai features
Choose Five9 if…
- your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
- use-case priority is contact-center and Dialpad is secondary for that motion
- You prioritize power dialer
- You prioritize crm / cti integrations
Overall recommendation
Comparison thesis: Overlapping use cases, different tradeoffs. Choose Dialpad only if your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape. Choose Five9 only if your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape. Workflow advantage: Dialpad leans business-phone, team-communication; Five9 leans contact-center, customer-messaging. Trade-off: you gain focus on one product's motion at the cost of the other's adjacent coverage — no universal winner. Dialpad is a poor fit when that limitation bites: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price Five9 is a poor fit when that limitation bites: 50 concurrent-seat minimum — not viable for small SMB phone buyers Hard limitation for Dialpad when it matters: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price. Hard limitation for Five9 when it matters: 50 concurrent-seat minimum — not viable for small SMB phone buyers. Neither product has a completed hands-on product test on SoftwareGlimpse — this comparison is research/data-based only. Pricing threshold: estimate spend with the cost calculator before shortlisting.
Key trade-off
Dialpad trades toward analytics; Five9 trades toward power dialer.
Winner by category
Only dimensions with researched evidence for this pair.
| Dimension | Winner | Why |
|---|---|---|
| Number / country coverage | Tie | Dialpad vs Five9 on number coverage: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to neither product on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. |
| Power dialer | Five9 wins | Dialpad vs Five9 on power dialer: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Five9 on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. |
| WhatsApp Business | Tie | Dialpad vs Five9 on whatsapp business: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to neither product on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. |
| CRM / CTI integrations | Five9 wins | Dialpad vs Five9 on crm integrations: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Five9 on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. |
| Routing & IVR | Tie | Dialpad vs Five9 on routing: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to neither product on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. |
| Reporting | Dialpad wins | Dialpad vs Five9 on analytics: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Dialpad on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. |
| AI features | Dialpad wins | Dialpad vs Five9 on ai features: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Dialpad on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. |
Side-by-side feature matrix
Normalized availability from product research — empty rows are not shown.
Voice
| Feature | Dialpad | Five9 |
|---|---|---|
| Cloud phone / VoIP | Strong | Strong |
| Call routing & IVR | Strong | Strong |
| Call recording | Strong | Strong |
| Power dialer | Moderate | Strong |
Messaging
| Feature | Dialpad | Five9 |
|---|---|---|
| SMS messaging | Strong | Strong |
| WhatsApp Business | Moderate | Moderate |
| Shared inbox | Moderate | Strong |
| Team messaging | Strong | Limited |
| Unified multichannel inbox | Moderate | Strong |
| Video meetings | Strong | Moderate |
Platform
| Feature | Dialpad | Five9 |
|---|---|---|
| CRM / CTI integrations | Moderate | Strong |
| Analytics & reporting | Strong | Strong |
| AI assistance | Strong | Strong |
Pricing comparison
Pricing evidence last checked Sep 10, 2026.
Dialpad
From $15.00/user/mo
- Connect Standard$15.00/user/mo
- Connect Pro$25.00/user/mo
- Connect EnterpriseCustom
- Dialpad Sell$39.00/user/mo
- Dialpad Support$80.00/user/mo
Five9
From $119.00/user/mo
- Digital$119.00/user/mo
- Core$159.00/user/mo
- PlusCustom
- ProCustom
- EnterpriseCustom
Seat-count estimates
Labeled estimates from verified starting per-seat pricing — not invoices.
| Seats | Dialpad | Five9 |
|---|---|---|
| 5 | ~$75.00/mo (5 × starting seat) | ~$595.00/mo (5 × starting seat) |
| 10 | ~$150.00/mo (10 × starting seat) | ~$1,190.00/mo (10 × starting seat) |
| 25 | ~$375.00/mo (25 × starting seat) | ~$2,975.00/mo (25 × starting seat) |
| 50 | ~$750.00/mo (50 × starting seat) | ~$5,950.00/mo (50 × starting seat) |
Estimate from verified starting per-seat pricing — actual total depends on plan, annual discounts, and add-ons.
Starting prices not verified for either product Model team cost scenarios in the business-communications cost calculator Cost calculator: /tools/business-communications-cost-calculator/
Best for
Scenario picks from researched strengths — not a universal ranking.
- → Depends
Prefer Dialpad when your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
Prefer Dialpad when your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
- → Depends
Prefer Dialpad when use-case priority is business-phone and Five9 is secondary for that motion
Prefer Dialpad when use-case priority is business-phone and Five9 is secondary for that motion
- → Depends
Prefer Five9 when your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
Prefer Five9 when your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
- → Depends
Prefer Five9 when use-case priority is contact-center and Dialpad is secondary for that motion
Prefer Five9 when use-case priority is contact-center and Dialpad is secondary for that motion
- → Dialpad
Best for analytics
Dialpad vs Five9 on analytics: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Dialpad on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above.
- → Dialpad
Best for ai features
Dialpad vs Five9 on ai features: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Dialpad on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above.
The differences that actually matter
Pair-specific analysis for Dialpad vs Five9 — not generic category copy.
WhatsApp Business
TieDialpad and Five9 are close on whatsapp business. Dialpad vs Five9 on whatsapp business: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to neither product on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above. Feature evidence also diverges on Power dialer (Dialpad: Moderate; Five9: Strong); Shared inbox (Dialpad: Moderate; Five9: Strong); Team messaging (Dialpad: Strong; Five9: Limited).
Power dialer
Five9 aheadOn power dialer, Five9 is ahead. Dialpad: Trails Five9 on this criterion. Five9: Dialpad vs Five9 on power dialer: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Five9 on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above..
Routing & IVR
TieDialpad and Five9 are close on routing & ivr. Dialpad vs Five9 on routing: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to neither product on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above.
CRM / CTI integrations
Five9 aheadOn crm / cti integrations, Five9 is ahead. Dialpad: Trails Five9 on this criterion. Five9: Dialpad vs Five9 on crm integrations: Dialpad and Five9 share buyer workflows; choose based on documented strengths and limits. Decision edge to Five9 on this criterion for this pair — unlike a generic feature matrix, the hinge is the buyer job above..
Pros and cons
Product-specific for this pair — derived from researched outcomes and editorial notes.
Dialpad
Pros
- Stronger on analytics
- Stronger on ai features
Cons
- Trails on power dialer
- Trails on crm / cti integrations
Five9
Pros
- Stronger on power dialer
- Stronger on crm / cti integrations
Cons
- Trails on analytics
- Trails on ai features
Who should not choose each product
Decision quality improves when we say who should walk away.
Don't choose Dialpad if…
- You need Five9's stronger power dialer more than Dialpad's strengths
- You need Five9's stronger crm / cti integrations more than Dialpad's strengths
- Your primary fit looks closer to: your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
- Your primary fit looks closer to: use-case priority is contact-center and Dialpad is secondary for that motion
Don't choose Five9 if…
- You need Dialpad's stronger analytics more than Five9's strengths
- You need Dialpad's stronger ai features more than Five9's strengths
- Your primary fit looks closer to: your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
- Your primary fit looks closer to: use-case priority is business-phone and Five9 is secondary for that motion
Alternatives worth considering
When neither product is the right fit.
Enterprise-grade UCaaS / cloud phone platform (RingEX) with deep call routing, video, team messaging and contact-centre options — Core from ~$20/user/month annual.
Mid-market cloud phone and customer-conversation platform with deep CRM/helpdesk CTI, IVR, power dialer on Professional, and paid AI add-ons — 3-licence minimum.
Meetings-first Workplace suite plus Zoom Phone UCaaS — Phone US/CA Unlimited research floor ~$15–16/user/month; free meetings/chat exist but Phone is paid.
SMB-friendly unified business communications — Core $15, Engage $25, Scale $75 per user/month annual, with messaging apps including WhatsApp and a Contact Center ladder from $75/agent.
Final verdict
Scenario-level close — not a repeat of the intro.
Dialpad wins when…
your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
Five9 wins when…
your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
- Prefer Dialpad when your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shapeDepends
- Prefer Dialpad when use-case priority is business-phone and Five9 is secondary for that motionDepends
- Prefer Five9 when your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shapeDepends
- Prefer Five9 when use-case priority is contact-center and Dialpad is secondary for that motionDepends
Which one should you choose?
Choose Dialpad if:
- your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape
- use-case priority is business-phone and Five9 is secondary for that motion
Choose Five9 if:
- your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
- use-case priority is contact-center and Dialpad is secondary for that motion
Product screenshots
Real product UI from our media library — no placeholders.
Dialpad
Five9
FAQ
- Is Dialpad better than Five9?
- Comparison thesis: Overlapping use cases, different tradeoffs. Choose Dialpad only if your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape. Choose Five9 only if your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape. Workflow advantage: Dialpad leans business-phone, team-communication; Five9 leans contact-center, customer-messaging. Trade-off: you gain focus on one product's motion at the cost of the other's adjacent coverage — no universal winner. Dialpad is a poor fit when that limitation bites: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price Five9 is a poor fit when that limitation bites: 50 concurrent-seat minimum — not viable for small SMB phone buyers Hard limitation for Dialpad when it matters: Pricing page is product-tab heavy — Connect vs Support vs Sell can confuse buyers comparing a single seat price. Hard limitation for Five9 when it matters: 50 concurrent-seat minimum — not viable for small SMB phone buyers. Neither product has a completed hands-on product test on SoftwareGlimpse — this comparison is research/data-based only. Pricing threshold: estimate spend with the cost calculator before shortlisting.
- Which business communications fits which team?
- Dialpad: your buying job matches “AI-first cloud phone (Dialpad Connect) with included transcription/summaries — Standard fr” rather than Five9's shape Five9: your buying job matches “Cloud contact center (CCaaS) — Digital from $119/concurrent seat/mo; Core $159; Plus/Pro/E” rather than Dialpad's shape
- Does Dialpad or Five9 have a free plan?
- Dialpad: No free plan. Five9: No free plan.
- How does Dialpad vs Five9 pricing compare?
- Dialpad starts from $15.00/user/mo. Five9 starts from $119.00/user/mo. Confirm live vendor pricing before purchasing.
- How did SoftwareGlimpse compare these products?
- We map both products to the same category criteria, then evaluate trade-offs using verified product, pricing and feature evidence. Affiliate relationships never change outcomes.
- reviewDialpad review
- reviewFive9 review
- pricingDialpad pricing
- pricingFive9 pricing
- alternativeRingCentral alternative
- alternativeAircall alternative
- alternativeZoom alternative
- guideWhat Is Business Communications Software? Beginner's Guide
- guideHow to Choose Business Communications Software: Job-First Framework
- guideBusiness Communications Pricing Guide: Seats, Minutes & Message Fees
- categorybusiness communications hub
- finderBest communications software
- calculatorCost calculator
Related comparisons
Alternatives to consider
RingCentral
Enterprise-grade UCaaS / cloud phone platform (RingEX) with deep call routing, video, team messaging and contact-centre options — Core from ~$20/user/month annual.
Aircall
Mid-market cloud phone and customer-conversation platform with deep CRM/helpdesk CTI, IVR, power dialer on Professional, and paid AI add-ons — 3-licence minimum.
Zoom
Meetings-first Workplace suite plus Zoom Phone UCaaS — Phone US/CA Unlimited research floor ~$15–16/user/month; free meetings/chat exist but Phone is paid.
Nextiva
SMB-friendly unified business communications — Core $15, Engage $25, Scale $75 per user/month annual, with messaging apps including WhatsApp and a Contact Center ladder from $75/agent.
Still deciding between Dialpad and Five9?
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