DE Toolkit Onboarding Checklist
Checklists

Onboarding Checklist

Onboarding Checklist — Deployment Engineer

Owner: Manager running the onboarding. Estimated time: 3–4 business days for Sections 1–5. Sections 6–8 unfold over weeks 1–4. Print this. Check off physically. A missed step in week 1 becomes a missed deliverable at Day 30.


Section 0 — Pre-Day-1

  • Offer letter signed, start date confirmed
  • Compensation structure reviewed (base, on-call stipend if applicable, performance bonus)
  • Laptop procured and configured
    • OS up to date, disk encryption enabled
    • 1Password or equivalent password manager installed
    • Python 3.11+ installed and confirmed: python3 --version
    • Git installed and configured
    • Slack app
    • Zoom app
    • SSH key generated — public key shared with manager for lab access
  • Welcome email scheduled for 8am Day 1

Section 1 — Systems Access (Day 1, morning)

Identity and access

  • Google Workspace account provisioned
  • Email signature configured (CMTG brand, phone, LinkedIn)
  • 2FA / MFA enforced on all Google accounts
  • Calendar shared with manager

Core platforms

  • HubSpot user created — permissions: Contacts/Companies/Deals write, Reports read
  • HubSpot owner ID assigned and recorded: ________________
  • Supabase access confirmed — avaya.cloudmagicgroup.com/portal loads correctly
  • n8n access confirmed — https://n8n.cloudmagicgroup.com loads, credentials working
  • Splunk access configured — either VPN/SSH tunnel to ThinkPad or direct LAN access

Project environment

  • GitHub access — added to Cloud-Magic-Technology org
  • Repository cloned: git clone git@github.com:Cloud-Magic-Technology/avaya.git
  • .env file provisioned with required credentials (copy from manager’s secure share, not from repo)
  • Python dependencies installed: pip install -r requirements.txt
  • Test script run successfully: python3 execution/compliance_checker.py --industry healthcare

Slack channels joined

  • #migrations
  • #sales-alerts
  • #hot-leads (read-only)
  • #competitive-digest (read-only)
  • #general
  • #it-ops (if exists)

Lab access (SSH)

  • SSH key added to ThinkPad: ssh-copy-id thinkpad
  • SSH key added to Surface: ssh-copy-id -J thinkpad n8n@10.1.50.206
  • Connectivity confirmed: ssh thinkpad "echo connected"
  • n8n surface connectivity confirmed: ssh -J thinkpad n8n@10.1.50.206 "echo connected"

UCaaS platform access

  • RingCentral partner portal access granted (partners.ringcentral.com)
  • 8x8 partner access granted
  • Net2Phone partner access granted
  • CBTS / Webex partner hub access granted (admin.webex.com)
  • AireSpring partner access granted (via channel manager)
  • XTIUM partner portal access granted

Section 2 — Document Handoff (Day 1, afternoon)

Walk through the toolkit index together — don’t just drop a link.

  • deployment-toolkit/README.md — walk through the read-in-order table
  • Explain the 3-layer architecture (directives → you → execution scripts)
  • Show where directives live: directives/migration-workflow.md
  • Show where execution scripts live: execution/
  • Show Google Drive structure for customer-facing documents

Verify comprehension (end of Day 1)

Have them summarize back in 3 minutes each:

  • The 7 migration stages and what they own in each (from 02-the-migration-lifecycle.md)
  • The porting lifecycle end to end (from 04-number-porting.md)
  • The analog device problem and why it matters (from 03-assessment-and-discovery.md)

Section 3 — Shadow + Practice (Days 2–5)

Recorded migration review

  • Review recording or walkthrough of one completed full assessment
  • Review recording or walkthrough of one cutover execution (or run a dry-run with manager)
  • Debrief: what stood out, what questions do they have

Live CLI practice (Day 2–3, in sandbox environment)

Walk through each CLI tool against a test migration ID:

  • porting_tracker.py — create a test order, advance stages, generate checklist
  • compliance_checker.py — detect a vertical, check status, sign off a requirement
  • feature_mapper.py — generate a feature gap report for RingCentral and 8x8
  • health_check.py — run a health check with test metrics
  • generate_proposal.py --stage assessment — generate the assessment questionnaire

Platform provisioning sandbox (Day 3–5)

In a partner sandbox account (not a live customer account):

  • Create a test tenant on RingCentral
  • Import 5 test users via CSV
  • Configure a 2-level auto-attendant
  • Configure a hunt group with 3 members
  • Set up voicemail-to-email for one test user
  • Set an E911 address and run the verification
  • Repeat on 8x8

Section 4 — First Live Activity (Week 2)

Co-pilot a real assessment

  • Assigned as co-pilot on an in-progress migration (manager or senior DE leads)
  • Takes notes on all 8 assessment sections
  • Submits the porting order LOA under supervision
  • Writes the assessment summary document (reviewed by senior DE before sending)

HubSpot hygiene confirmed

  • Every deal they touch has a “Next Step” with a date
  • Every deal they touch has an updated Notes field
  • Confirmed the deal stage matches what’s in Supabase

Section 5 — Business Operations (Day 3–5)

  • Employee handbook acknowledged
  • NDA signed
  • Background check completed (if required for customer-facing access)
  • Security awareness training completed (if required by compliance program)
  • Data handling policy reviewed: customer data stays in approved systems (Supabase, HubSpot, Google Drive) — not in personal storage

On-call expectations

  • On-call rotation policy reviewed (is there one? What is the expectation for cutover coverage?)
  • Emergency escalation path documented: who to call at 3am when a port fails
  • Personal cell number shared with manager (for cutover night communication)

Section 6 — Week 2 Checkpoint

  • All systems access confirmed working (test each one)
  • First assessment co-piloted — debrief completed
  • At least 1 porting order submitted (supervised)
  • First UCaaS platform provisioning sandbox completed (RingCentral or 8x8)
  • Any open questions from primer docs resolved

Section 7 — Week 3–4 Ramp Checkpoints

End of week 3

  • Assessment completed independently on a real migration
  • All CLI tools used without reference to docs
  • First cutover co-piloted (they run the checklist; senior DE observes)
  • Compliance gate process completed on at least 1 migration

End of week 4

  • Assessment completed: ≥2 independently
  • Platform provisioning: comfortable on RingCentral and 8x8 independently
  • Porting order: at least 1 LOA accepted on first submission
  • First solo cutover completed (senior DE on call, not in the room)
  • Full Day 30 review against 10-30-60-90-plan.md

Section 8 — Day 30 / 60 / 90 Formal Reviews

Day 30

  • Formal 60-minute review — metrics vs. plan
  • Platform proficiency self-assessment (1–5 scale, each platform)
  • Feedback on toolkit gaps — what’s missing or wrong?
  • Confirm all access is still working

Day 60

  • Formal 60-minute review — metrics vs. plan
  • At least 1 solo cutover completed cleanly
  • Identify weakest platform — schedule focused practice time
  • Upsell opportunities identified and routed to sales?

Day 90

  • Full performance evaluation
  • Platform proficiency review — formal rating per platform
  • Compensation review if applicable
  • Specialty track discussion (contact center, compliance, enterprise, platform specialist)
  • Confirm they’ve completed the formal assessment (assessment/deployment-engineer-assessment.md)

Section 9 — Things That Get Missed

Lessons from past onboardings. Add here when you find new ones.

  • Python environment: confirm they’re using the correct Python version with all dependencies — which python3 should point to 3.11+, not system Python
  • .env file: they need to source it in every terminal session, or add it to their shell profile — otherwise CLI scripts fail silently
  • E911 test: new DEs often skip the 933 test because they assume the platform handles it — it doesn’t automatically. Make sure they do this physically on every migration
  • Port-day escalation numbers: must be written down before cutover, not searched for at 3am. Make them fill out the contact card template before every cutover.
  • Fax inventory: new DEs trust the customer’s self-report. They almost always miss at least one fax machine. Require a physical walkthrough or a confirmed “no fax machines anywhere in the building” from the IT admin.
  • SIP ALG: many DEs fix call quality issues by changing platform settings without checking SIP ALG first. SIP ALG is the cause of ~30% of call quality issues. Make it the first thing they check.
  • Supabase migration ID: the HubSpot “Migration ID” field must match the migration_id in Supabase exactly. Mismatch means CLI scripts and n8n can’t find the migration. Verify this at assessment completion.

Section 10 — Signoff

  • DE confirms all systems access is working: _______________________ (date + sig)
  • DE confirms they’ve completed all 10 primer docs: _______________________ (date + sig)
  • DE confirms they’ve completed the assessment exam: _______________________ (date + sig)
  • Manager confirms onboarding complete: _______________________ (date + sig)
  • Checklist filed in Drive: Cloud Magic › HR › Onboarding › [DE Name] › 2026-XX-XX-DE-Onboarding-Complete.pdf