Best Practices for Automating Sales Follow-Ups

Most teams obsess over the 5% who reply. But what about the other 95%? That’s where your investment lives. You spent real time (and real money) building that list: → Enrichment tools → Research → Personalization → Manual review And then… No reply? No interest? Off to the next batch? The best operators treat every reply—yes, no, or silence—as a chance to learn, improve, or close the loop. That’s where automation shines: → Out-of-office replies? Route them into a “Back to Work” campaign timed to their return → “Not a fit” replies? Offer a referral link with affiliate commission → Total silence? Trigger a 90-day re-engagement path with new angles or case studies → Ghosted after showing interest? Schedule soft nudges before archiving → Unsubscribes? Instantly tagged and blocked from future sends None of this needs to be manual. It just needs to be mapped—and automated—with intent. Because if your outbound system treats non-responders like throwaways… You’re burning time and money. The real cost isn’t in outreach. It’s in letting 95% of your effort go nowhere. — 🔔 Follow Nathan Weill for automation strategies that turn missed chances into second ones. #OutboundOps #SalesAutomation #NoCode #LeadFollowUp #Zapier #OperationalExcellence #RevenueOperations

This one’s for Founders & Sales folks. I built an AI agent that cut my sales follow-up time by 90%. Not kidding. From 30 minutes per email... to 2 minutes. And I actually enjoy it now. Let me back up. I hate writing sales follow-ups. → Re-reading call notes → Trying to remember context → Spending hours wordsmithing Even with my system of organized ChatGPT folders with custom deal context, it still took forever. So I did what any founder would do. I built a tool. It sounds much harder than it actually was. I hadn’t built an AI agent before and it only took me 2 hours end to end. Here’s what I used and how it works. ⚙️ Built with: Relay.app (shoutout to Jacob Bank - love what you’re building!) Step 1: I trigger Relay to follow up with a particular deal in Hubspot. Step 2: Relay retrieves deal context from Hubspot (it’s made me much more diligent about making sure my data is up-to-date here) Step 3: Agent reviews the deal and decides if a follow-up is needed. It gives me the following output: Is a follow up required? Yes / No response What kind of follow-up is required? General check-in email, breakup email, nudge with resources (I provided these options for it to choose from). Why did it make this decision? This is really helpful because it gets me up to speed on the deal quickly—when did we last check in, what were their objections or concerns, when is the next expected touch point, and so on. Step 4: I approve or tweak. I tell the agent if it’s right or wrong, or provide context it may not have. Step 5: AI writes a draft email. The first draft hits me within ~20 seconds. I give high-level feedback (e.g., “focus more on timeline urgency”) if necessary. Step 6: AI revises the draft based on by input. At this stage I have an almost perfect draft. I make minor edits if at all and hit send. The whole process takes 2–3 minutes max. Are we all getting replaced by AI in 2 years? Probably. But for now, I’ve outsourced an annoying part of sales and it's amazing.

Here's exactly how I structure my follow-ups to stop deals from slipping or ghosting at the last minute. Buyers ask themselves 5 crucial questions before they spend money. So we match our follow ups to each different question of the buying journey. The questions: 1/ "Do we Have a Problem or Goal that we Urgently need help with?" Follow up examples: Thought Leadership emphasizing the size / importance of the problem. Things like articles from Forbes, McKinsey, HBR or an industry specific publication. Screenshots, summations or info-graphics. NOT LINKS. No one reads them. 2/ "What's out there to Solve the Problem? How do Vendors differ?" Follow up examples: Sample RFP templates with pre-filled criteria. Easy to read buying guides. Especially if written by a 3rd party. 3/ "What Exactly do we need this Solution to do? Who do we feel good about?" Follow up examples: 3 bullets of criteria your Buyers commonly use during evaluations (especially differentiators.) Here's example wording I've used at UserGems 💎: "Thought you might find it helpful to see how other companies have evaluated tools to track their past champions. Their criteria are usually: *Data quality & ROI potential *Security (SOC2 type 2 and GDPR) *How easy or hard is it to take action: set up/training, automation, playbooks Cheers!" 4/ "Is the Juice worth the Squeeze - both $$$ & Time?" Follow up examples: Screenshots of emails, texts or DMs from customers talking about easy set up. Love using ones like the Slack pictured here. Feels more organic and authentic than a marketing case study. 5/ "What's next? How will this get done?" Follow up examples: Visual timelines Introductions to the CSM/onboard team Custom/short videos from CSM leadership When we tailor our follow ups to answer the questions our Buyers are asking themselves - Even (especially!) the subconscious ones Our sales cycles can be smoother, faster and easier to forecast. Buyer Experience > Sales Stages What's your best advice for how to follow up? ps - If you liked this breakdown, join 6,000+ other sellers getting value from my newsletter. Details on my website!