Pool Service Software Buyer's Checklist

Print this, or save it to PDF (File → Print → Save as PDF). Walk into every demo with these questions.

Phase 1 — Internal alignment (before contacting vendors)

  1. How many techs / routes do we currently run?
  2. How many techs / routes do we expect in 12 months?
  3. Is pool our only trade, or do we do lawn / cleaning / pressure washing?
  4. Is chemistry tracking core to our value prop, or generic?
  5. Is QuickBooks integration a hard requirement?
  6. Do we have recurring service contracts to manage?
  7. What's our hard ceiling on monthly software cost?

Phase 2 — Questions to ask every vendor on the demo

Pricing & total cost

  1. What's the cheapest plan that supports our route count and tech headcount?
  2. What's the per-user / per-route escalation as we grow?
  3. Are there implementation or setup fees? How much?
  4. What's included vs paywalled in our quoted plan?
  5. What's the annual discount, and the cancellation policy?
  6. What's payment processing fee (Stripe, ACH, card)?

Features & workflows

  1. How does chemistry tracking work? Is LSI calculator included at our tier?
  2. Does route optimization recalculate daily, or is it static?
  3. Does the customer portal handle invoices, chemistry reports, AND payments?
  4. How does the mobile tech app handle no-signal conditions?
  5. What QuickBooks integration depth is provided (one-way sync vs bidirectional)?

Operations & support

  1. What's the typical onboarding period for a business our size?
  2. What does ongoing support look like? Hours, channels, response time?
  3. Can we get 2-3 reference customers in our size + region?
  4. What's your data export policy if we leave?
  5. Where's your roadmap published? Any new features releasing this quarter that affect us?

Phase 3 — Migration plan (once you've chosen)

  1. Week 1: Data prep. Export customer list, route definitions, recurring billing setup from current system.
  2. Week 2: Setup & configuration. Create your account, import customers, configure billing, set up techs, configure chemistry parameters.
  3. Week 3: Parallel run. Run both systems concurrently. Verify routes match, billing posts correctly, photo documentation works.
  4. Week 4: Cutover. Stop using the old system. Close out any remaining invoices. Keep a 30-day backup of the old data.
  5. Week 6-12: Optimization. Re-train techs on advanced features. Configure automations, customer-facing branding, custom job forms.

Red flags to walk away from

  • Demand for annual contract before any evaluation period
  • Won't show pricing until late in the sales cycle
  • Implementation fee "depends on discovery" — no published range
  • No clear data export path
  • Custom development required for basic features ("we can put that on our roadmap")
  • Refuses to provide reference customers in your size segment
  • Limited or evasive on cancellation policy
  • Sales rep doesn't know answers to basic technical questions

This checklist is part of StackMatch — independent software comparisons for service businesses. See the full buyer's guide, the ranked vendor shortlist, or our methodology.