You have 1,200 past customers sitting in a spreadsheet. Someone told you "email marketing" is the answer, so you're comparing Mailchimp and ConvertKit feature lists — templates, A/B testing, landing pages — none of which is the actual job. The actual job: twice a season, send the right email to the right segment of past customers, and book jobs from people who already trust you. Here's the honest tool pick for that job.
Start with the reactivation campaign playbook (Pillar D) — the strategy this tooling serves. This comparison sits inside the 8-system framework, alongside lead capture, estimate follow-up, reviews, and scheduling.
What contractors actually need from email (it's a short list)
- Segment the list — by trade-relevant slices: last service date, equipment age, maintenance-plan status, zip code. "Everyone who had an install 2+ years ago and no maintenance plan" is a campaign; "all contacts" is spam.
- Send seasonal campaigns — the spring tune-up push, the fall furnace check, the storm-season inspection offer. Two to four campaigns a year, well-targeted.
- Automate the basics — the welcome email for new customers, the post-job thank-you, the annual check-in. Set once, run forever.
- Stay compliant without thinking — one-click unsubscribe, physical address in the footer, consent records. Non-negotiable.
Notice what's not on the list: fancy templates, complex funnels, e-commerce features. Contractors need a mailing list with segments and automations, not a marketing department.
Mailchimp: the default (fine, with caveats)
- Free tier historically covers up to 500 contacts — enough for a small shop's first reactivation campaigns at $0. Verify current limits; they change.
- Segmentation is decent — tags and segments handle the trade-relevant slices above.
- Automation exists but the good stuff is gated. Multi-step customer journeys live on paid tiers. The free plan sends campaigns; the paid plans run systems.
- Pricing scales with contacts, which punishes the exact behavior you want — growing your list. A 5,000-contact list costs real money monthly.
- Best for: the shop starting from zero that wants to send its first two seasonal campaigns free, then evaluate.
ConvertKit (now Kit): the creator's tool (usually wrong for contractors)
- Excellent automation and deliverability — genuinely the best email engine of the three for newsletters and sequences.
- Built for creators, not contractors. The mental model is subscribers and broadcasts, not customers and segments. No native concept of "last service date" or "equipment age."
- Free tier historically covers up to 1,000 subscribers — generous, but you're fitting a square peg in a round hole.
- Best for: almost never the contractor pick. If you're already on it for another reason, it works — but don't migrate to it for reactivation.
GoHighLevel: the "you're already paying for it" answer
- If you run GHL for texting/automation ($97/mo Starter), the email is included. Same contacts, same segments, same automations — email becomes one more channel in the system you already own, not a separate tool with a separate list.
- Unified segmentation is the killer feature. The segment "no maintenance plan + last service 18 months ago" already exists for your texts; the email campaign just uses it. No syncing, no duplicate lists, no drift.
- Email deliverability needs setup — dedicated sending domain, SPF/DKIM records (the authentication that proves your emails are really from you). GHL walks you through it, but it's a real 30-minute task. Skip it and your campaigns land in spam.
- Best for: any shop already on GHL. Don't buy a separate email tool — use the one inside the system.
The honest pick (it's simpler than the comparison suggests)
- On GoHighLevel already → use GHL email. No separate tool, no synced lists, one segmentation system. This is the right answer for most shops reading this blog.
- Not on GHL, small list (under ~500) → Mailchimp free. Send your first seasonal campaigns, prove the channel books jobs, then decide whether to upgrade or consolidate into GHL.
- Not on GHL, bigger list, no automation platform → Mailchimp paid or GHL. At this point compare Mailchimp's contact-based pricing against GHL's flat $97/mo — GHL usually wins once the list passes a few thousand, because you also get the texting and automation.
The compliance footer (every campaign, every tool)
- One-click unsubscribe in every marketing email. Not "reply to unsubscribe" — a link.
- Physical address in the footer (CAN-SPAM requirement). A PO box works.
- Consent records: only email people who gave you their address in a business context (customers, quote requesters). Purchased lists are illegal for this purpose and destroy deliverability.
- Honor unsubscribes immediately and keep the suppression list forever — even across tool migrations.
The full CAN-SPAM walkthrough is in CAN-SPAM for contractor email campaigns. This is general information, not legal advice.
The first-campaign blueprint (week one, step by step)
Don't start with a newsletter. Start with the campaign that pays for the tool: the dormant-customer reactivation. The blueprint:
- Build the list: export customers with no job in 12+ months (and no open estimate). Clean it: dedupe, remove bad addresses, suppress anyone who unsubscribed from anything. Expect the list to shrink 10–20% — that's hygiene working.
- Write the email (150 words max): a personalized subject line, one paragraph acknowledging the gap since their last service, one offer (the seasonal tune-up special), one clear CTA button ("Book my tune-up"). Sign it from the owner, not the brand. The two lines that do the heavy lifting:
Subject: [First Name], quick check on your [system type]
It's been a while since we serviced your [equipment]...
- Send Tuesday or Wednesday, 9–11am recipient local time. Avoid Mondays (inbox pile) and Fridays (checked out).
- The follow-up is the campaign: non-openers get a different subject line 5 days later; openers-who-didn't-click get the SMS nudge on day 7 (with opt-out language, inside quiet hours). Most reactivation revenue comes from the follow-ups, not the first send.
- Measure three numbers: booked jobs (the only one that matters), unsubscribe rate (health check — a sudden spike means something is wrong with the list or the content), and spam complaints (zero tolerance — investigate any). Ignore open rates as a success metric; they're directional at best with current privacy changes.
Run this one campaign before building anything else. If it books jobs, you have your email program. If it doesn't, the problem is the list or the offer — not the tool.
Example: the $0-to-first-campaign path
Example: A 2-truck plumbing shop has 900 past customers in a spreadsheet and no email tool. They import the list to Mailchimp's free tier, segment "no service in 18+ months" (340 contacts), and send the fall water-heater flush campaign — one email, one clear offer, one booking link. It books 11 jobs. Total cost: $0 and an afternoon. The next quarter they move to GHL, import the list once, and the same segment becomes a text + email sequence. The tool changed; the asset — the segmented list — carried over. That's the point: the list is the asset, the tool is the envelope.
Related guides in this series
The strategy is the reactivation campaign playbook. For the seasonal campaigns themselves, the fall furnace tune-up campaign and summer AC maintenance reminders. For list hygiene before you send, how to clean your customer list. And the framework is the 8-system framework.