From Awkward to Effective: Using AI to Sell Without Feeling Gross

By Summer Poletti: I am the founder of Rise of Us, host of Revenue Remix podcast, and a fractional revenue leader. I help early growth-stage companies scale smarter—by aligning growth strategy, AI-enabled workflows, and human connection. I equip teams to harness automation without losing sight of security, ethics, or the buyer at the center. I help salespeople spend less time on admin, run shorter meetings, and create sales playbooks they actually use.

AI Image, Made with ChatGPT

Inspired by a conversation during #wxaisocialsaturday, I decided to do a deeper dive. By the way, if you’re not joining the conversation each Saturday, you’re missing out.  How can AI help my sales function?

Whether you’re still in your “I do all the things” era or you’re getting ready to hire your first sales person/team, this one’s for you.

Let’s start with a basic truth: AI is a transformational technology like the world hasn’t seen for generations. The new industrial era! AND it makes mistakes or completely fabricates things.

Think about it. You’re an expert in your field, so when you review AI output you know how to spot the hallucinations. 

Well, I’m an expert in sales and customer experience and I know how to spot mistakes or just bad advice from an AI tool. 

If you’re a founder, you didn't start your company because you love sales,but here you are: booking demos, writing follow‑ups, and hustling for revenue all while building the product.

And the buyers? They’ve changed too. By the time they talk to you, they’ve done their homework and they expect more than a generic scripted pitch.

And here’s something else they won’t tell you - if you build it, they won’t come. Inbound-only isn’t enough anymore. You’ll need to do outbound, too. It can feel awkward or unclear where to start, but that’s where AI can help.

Your LLM can suggest sequences, write follow-ups, even generate outbound ideas. But remember: it pulls from what’s already out there on the internet. And let’s be honest, there’s a lot of annoying, outdated, or flat-out wrong sales advice floating around.

Have you ever spoken to a salesperson who made you cringe? So has your AI.

So in this blog, we’ll cover:

• What AI Can’t Do for Sales (and why it matters)

• What AI Can Do (and how to make it work for you)

• A Simple Framework for How to Start Smart

• Success Stories from the Front Lines

• Make Sales Work With You Not Against You

  
  

What AI Can’t Do (and Why It Matters)

Let’s be clear: AI can help you get started faster. It can save you hours, especially when you’re juggling a million things. But AI doesn’t know your buyer the way you do. And it doesn’t know how you want to sell.

Here’s where it falls short:

• It doesn’t understand nuance. AI can’t read the room on a Zoom call. Even if there’s “coaching” built into the tool. It won’t catch the awkward pause, the shift in a buyer’s tone, or the raised eyebrows. That’s on you.

• It can’t build relationships. People buy from people they trust. Trust is built over time with follow-up, consistency, showing you care about THEM, and being genuinely helpful. No tool can do that for you.

• It’s not a strategist. AI can generate outreach messages, with the right prompting, but it can’t decide who you should be talking to, when, or why. That part still requires human judgment and a clear understanding of your buyer.

• And some of the advice it gives? Just bad. Most LLMs are trained on the internet, which means they’ve absorbed a lot of outdated or downright cringey sales scripts. If you’ve ever been on the receiving end of one of those “Just checking in to see if you got my last email” messages, you know what I mean.

  
  

Here’s the fix: You can absolutely use AI to move faster but only if you give it clear direction, guardrails, and your unique voice. That starts with knowing your buyer, your product, and what kind of experience you want people to have when they engage with you.

What AI Can Do (and How to Make It Work for You)

Running founder-led sales or transitioning to your first sales person/team? AI is like having a sales assistant who never sleeps, but only if you train it right.

Here’s where I’ve seen AI deliver real value for founders trying to grow sales:

• Lead Qualification — without wasting your time AI can help you spot early red flags, ask better questions, and stop chasing people who were never going to buy. You can prompt it to simulate buyer objections or surface gaps in your discovery flow.

• Meeting Prep — that actually saves you time You don’t need 30 minutes to prep. A well-crafted prompt can give you talking points, insight summaries, or call questions in 7 seconds (I tested it). So you show up focused, not frazzled.

• Admin Automation — the sales hygiene you’ll actually do From call notes to follow-up drafts, let AI handle the busywork. This is how you keep your pipeline clean without sinking half your day into your CRM.

• Just-in-Time Sales Coaching — even if you’re not a sales pro AI can walk you through common objections, suggest phrasing, or surface past email threads  like a coach in your pocket. If you train it well. (More on that later.) Just don’t outsource your entire strategy to it. (More on that too.)

• Outbound Messaging — with a giant caveat Yes, your LLM can write sequences. But it’s pulling from what’s already on the internet  which includes a lot of outdated, cringe-worthy sales tactics. If you’re not careful, you’ll end up sounding like a pushy 2014 bro who sends “just bumping this to the top of your inbox” emails.

  
  

Pro tip: If outbound feels awkward, you’re not alone. Founders often don’t know what to say, when to say it, or how to stand out. That’s where a trained GPT, tailored to your ideal customer profile (ICP) and voice, can help. I help clients build these all the time — AI that writes like you, for your buyer, in your tone.

A Simple Framework to Start Smart (and Sound Like a Human)

You don’t need a 15-tool tech stack or a 90-day rollout plan. You just need a smart place to start and a way to avoid sounding like every other founder trying to sell.

Here’s how I coach early-stage teams:

1. Start with one real goal or objective

Not “get more sales,” but something specific:

• Qualify leads faster

• Run better sales calls

• Follow up more consistently

• Stay top of mind with prospects

This helps you figure out what kind of help you actually need.

2. Define your buyer before you define your messaging

• You need to know who you're selling to and what they care about.

• What's your ICP?

• What problems are they trying to solve? And the impact?

• How do you help them better or differently than your competitor - why do they choose you?

• What kind of outreach would actually resonate?

• What’s their AI tolerance?

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Don’t guesstalk to customers, listen to calls, look at deal data. Build your persona from real signals, not assumptions. And make sure your whole team agrees with the persona before you move forward. 

Pro tip: Work with someone who understands real sales theory to help you build a custom GPT or prompt set. That way, the messages you generate work. AI really loves “I hope this finds you well.”

A custom GPT trained on your buyers and good sales theory will produce tailored, relevant messaging that sounds like you while hitting what your buyer actually needs to hear.

3. Use what you already have

Tools like Notion, HubSpot, or Zoom often have built-in AI features that can help you prep for meetings, summarize calls, or draft follow-ups. Use those before buying something new.

4. Test one process, not your whole system

Try using AI to:

• Plan a cold outbound sequence

• Write outbound emails

• Help you anticipate and manage objections

• Write a follow-up after a demo

• Summarize a call so you’re not taking notes live

Keep it small and manageable, then iterate.

5. Gut-check the advice

If the messaging feels robotic, pushy, or too templated it probably is. That’s where your judgment (or a sparring partner) comes in. Don’t let your LLM write your entire GTM motion. Use it to accelerate what works, not copy what doesn’t.

The best way to gut check? Take a step back and ask yourself:  would I reply to this email?

Success Stories from the Front Lines (Even If You're Not a Sales Expert)

Case 1: Founder Who Wanted Out of Sales (But Still Wanted Results) A financial services founder was ready to step out of founder-led sales, but didn’t have time to manage a new rep. We built a Smart Sales Playbook — mobile-friendly, AI-powered, and embedded where the rep worked. Trained on their buyer persona and my sales philosophies.

Now the rep brags to his friends that he has “a sales coach in my pocket.”

• He qualifies faster

• Runs shorter meetings

• Closes more because he’s focused on people who are actually serious

  
  

Case 2: Lean SaaS Team With No Time to Sell An early-stage SaaS team was drowning in leads but had no bandwidth to follow up. We built an “AI SDR”:

• Automated nurture with video + email

• Follow-up for stalled deals

• Messages tailored by funnel stage

• Leveraging the right marketing content at the right time

It warmed leads until the founder could step in without pretending to be human or spamming anyone. And helped weed out the looky-loos because the founder was very excited to show people what she built and had a tough time determining who was serious and who was just curious.

These weren’t 6-month enterprise overhauls. They were smart, lightweight systems that helped real founders free up time, stay in control, and keep revenue moving.

Make Sales Work With You, Not Against You

AI won’t close deals for you. But it can give you time back and help you sell in a way that feels aligned with how you actually want to grow.

Whether you’re still doing founder-led sales or preparing to hand it off, the smartest time to build a system is before you're overwhelmed. One that:

• Matches how your buyers actually buy

• Trains your tools to sound like you

• Helps future hires hit the ground running

  
  

By the way, this is what I do. I work with early-stage SaaS and fintech companies to set up sales systems powered by smart tech, not bloated stacks. Sometimes I build from scratch. Sometimes I help founders get out of the sales seat without losing momentum. I also advise a handful of startups (including some backed by this very community).

And if you’re curious about how other founders think through these decisions, check out the Revenue Remix podcast. Many of my guests come straight from the WOMEN x AI ecosystem.

Let’s make sales feel less like a burden—and more like a lever.

Want more from Summer? Check out our recap of WxAI's Virtual Ignite Talks she hosted.