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Migration Guide5-step planUpdated May 25, 2026

Migrating from Streak to Outsolvi

Someone migrating from Streak is replacing a Gmail-native CRM, not just a tracker. The migration is more involved because pipelines, deal stages, and contact records need to land in a replacement CRM (HubSpot CRM Free is the canonical destination), and the tracking layer (Outsolvi) is added alongside.

Streak is a Gmail-native CRM with tracking bundled in. Migrating from Streak means two things: pick a replacement CRM (HubSpot CRM Free, Pipedrive, or another) and pick a tracking layer (Outsolvi). The combined cost of Outsolvi + HubSpot CRM Free is roughly 1/3rd of Streak Pro at $59/user/mo yearly and gives you confidence-scored tracking plus native Outlook + Gmail (Streak is Gmail-only).

The migration is structured as: Day 0 prep with pipeline export and replacement-CRM selection, Day 1 install Outsolvi + set up replacement CRM, Day 7 import pipeline data into the new CRM and configure webhook, Day 14 cutover from Streak to new stack, Day 30 cancel Streak. Total timeline is longer than Mailtrack migration (because CRM transition is involved) and shorter than enterprise Salesforce migrations.

Pre-migration checklist (Day 0)

  • Export Streak pipelines as CSV via Streak → Settings → Export. Each pipeline exports separately.
  • Export contact and deal data as CSV for import into the replacement CRM.
  • Select replacement CRM: HubSpot CRM Free is the canonical low-cost choice for most teams. Pipedrive ($12-$59/user/mo) is the alternative for teams who want a more sales-pipeline-focused UI than HubSpot's. Salesforce is overkill for most Streak-migrating teams.
  • Document Streak's custom fields and any Streak-specific workflows that need recreation in the new CRM.
  • Identify Outlook expansion needs — Streak is Gmail-only, so teams adding Outlook reps need the Outsolvi Outlook add-in.

Day-by-day migration plan

Day 0

Prep and CRM selection

Pipeline export complete, replacement CRM selected, custom-field mapping documented.

Tasks
  • Pipeline CSV exports complete
  • Contact and deal CSV exports complete
  • Replacement CRM selected and account created (HubSpot CRM Free is free; Pipedrive starts at $12/user/mo)
  • Custom-field mapping documented
Day 1

Install Outsolvi + configure replacement CRM

Both Streak and Outsolvi can run alongside each other temporarily. Set up the replacement CRM separately and start populating it from the CSV exports.

Tasks
  • Outsolvi Gmail extension installed
  • Outsolvi Outlook add-in installed for any Outlook reps
  • Replacement CRM account configured with custom fields matching Streak
  • Initial pipeline structure set up in replacement CRM
Day 7

Pipeline data import

Import contact and deal CSVs into replacement CRM. Configure Outsolvi → replacement CRM webhook so engagement events start flowing.

Tasks
  • Contact CSVs imported into replacement CRM
  • Deal CSVs imported with stage mapping
  • Outsolvi → CRM webhook configured (HubSpot or Pipedrive integration)
  • Test engagement events flowing into CRM activity timeline
Day 14

Workflow cutover

Team starts using the new CRM as the system of record. Streak remains read-only for reference but new deals and pipeline updates happen in the new CRM.

Tasks
  • Team training on new CRM workflows
  • Documentation updated to reflect new stack
  • Active deals moved from Streak to replacement CRM
  • Outsolvi tracking confirmed firing across team
Day 30

Cancel Streak

Final Streak cancellation. Historical Streak data exported and archived locally.

Tasks
  • Final Streak data export and archive
  • Streak subscription cancelled
  • Team retrospective on new stack workflow

Common gotchas for Streak migrations

Problem

Streak pipelines have custom fields that don't map cleanly to HubSpot or Pipedrive defaults.

Solution
Create custom properties in the new CRM matching the Streak fields before importing. Both HubSpot and Pipedrive support extensive custom-property creation.
Problem

Team used to seeing pipeline inside Gmail (Streak's core experience) now has to use a separate CRM tab.

Solution
HubSpot and Pipedrive both have Chrome extensions that show CRM context inside Gmail. The experience isn't identical to Streak's full-pipeline-in-Gmail, but the contact-context view is similar.
Problem

Streak's mail merge functionality is gone after migration.

Solution
If mail merge is workflow-essential, pair Outsolvi with GMass (Gmail-native mail merge) or use HubSpot's marketing-side bulk-email if applicable. Most teams find Streak's mail merge was used 1-2x per quarter and a separate purpose-built tool covers occasional bulk-send better.
Problem

Cost gap is bigger than expected because team has been on Streak's free tier.

Solution
If on Streak free, the upgrade path is Outsolvi at $7-$20/user/mo yearly + HubSpot CRM Free (still free) = $7-$20/user/mo total. Not a free-to-free swap, but adds Outlook support, confidence-scored opens, and AI features.
Team rollout playbook

For teams of 3-5 reps, the 30-day timeline works. For teams of 5-15 reps, the timeline often extends to 45-60 days because CRM transition is more complex than tracking-tool transition. Phased rollout pattern: champions on Day 1, half the team on Day 14, remainder on Day 30. Full Streak cancellation at Day 45-60.

Risk mitigation

30+ day dual-run with full Streak features active. CRM migrations carry more risk than tracking-tool migrations because pipeline data integrity matters. Keep Streak active for the full transition and have a clear rollback path if the replacement CRM doesn't work for the team.

Frequently asked questions

Why migrate from Streak instead of staying with the all-in-one tool?+

Two main reasons. First, Streak is Gmail-only — teams adding Outlook reps need a different stack. Second, the realistic Streak tier for CRM features (Pro at $59/user/mo yearly) is roughly 3x the combined cost of Outsolvi Teams Pro + HubSpot CRM Free ($20/user/mo yearly + $0). For teams that don't need Streak-specific features (mail merge, all-in-Gmail UX), the migration saves meaningful per-seat cost.

Which replacement CRM is best?+

HubSpot CRM Free is the canonical choice for cost-conscious teams — zero cost, genuinely usable, integrates with Outsolvi cleanly. Pipedrive is the alternative for teams preferring a more sales-pipeline-focused UI ($12-$59/user/mo). Salesforce is overkill for most Streak-migrating teams (priced for enterprise).

Will pipeline data import cleanly into HubSpot or Pipedrive?+

Mostly yes. CSV imports for contacts and deals work cleanly. Custom fields require recreation in the new CRM before import. Deal-stage mapping needs manual setup. Plan 2-4 hours for a clean import.

Can I keep using Streak for some pipelines and Outsolvi for tracking?+

Not recommended long-term. Two-tool overhead defeats the cost-saving purpose of migration. The clean state is one CRM + Outsolvi for tracking.

Start your Streak migration today

14-day free trial of Outsolvi, no credit card. Run alongside Streak during the calibration period, then cutover when the data confirms the new tool works for your team.

Nate SummersCo-Founder, Outsolvi

Nate built Outsolvi after watching every email-tracking tool he had ever used lie to him about opens. Outsolvi runs Tier 1 to 5 confidence scoring on every open, native in Outlook and Gmail, so the number on the dashboard is one a rep can actually act on.

Last reviewed May 25, 2026Editorially independent

We update these pages when the underlying mechanics change — new mailbox-provider rules, new tracker behavior, new measurement gaps. The dates above are real revisions, not auto-touches.