Founders
min read

How a $100M+ Company Is Actually Using AI in Sales (Without Replacing Humans)

A firsthand breakdown of how a $100M+ company is actually using AI to rebuild go-to-market systems at scale, without replacing humans or relying on outdated sales playbooks.

INTRO

AI is forcing every founder and revenue leader to rethink their go-to-market motion. The problem is, most people are reacting in one of two bad ways.

They are either clinging to outdated 2010s sales playbooks that clearly are not working anymore, or they are swinging too far in the other direction and assuming AI will magically replace human sellers.

I recently sat down with Kris Rudeegraap, CEO of Sendoso, for one of the most honest conversations I have had on AI and sales. Sendoso is doing over $100M in revenue, and Kris is not theorizing about the future. He is living this every day.

This article breaks down how they are actually using AI at scale, where it works, where it does not, and what this means for founders trying to build a modern GTM motion.

WHAT YOU’LL LEARN

  • Why old sales playbooks are quietly killing pipeline
  • How Sendoso rebuilt outbound and inbound with AI
  • What AI should automate and what humans must still own
  • How AI changes what “good” looks like in sales roles
  • What founders should focus on if they want real GTM leverage

CONTEXT: WHY THIS MATTERS

Pipeline generation today is harder than it has been in years. Buyers are overwhelmed. Email inboxes are a disaster. Single-channel outbound barely moves the needle.

At the same time, AI has created a new kind of confusion. Founders are buying tools without changing how their teams actually operate. There is this assumption that if you add enough AI, you can somehow remove human effort from sales entirely.

That is not what is happening at companies that are winning.

What stood out in my conversation with Kris is that Sendoso rejected both extremes. They did not double down on outdated sales dogma. And they did not treat AI as a silver bullet.

They rebuilt GTM as a system.

THE REAL ISSUE: BROKEN PLAYBOOKS AND NAIVE AI EXPECTATIONS

One thing Kris and I aligned on quickly is that most teams are stuck between two bad mental models.

The first is the predictable revenue era mindset. Spray-and-pray outbound. Overstaffed SDR teams doing manual work. Hoping volume solves everything.

The second is the belief that AI alone will fix the problem. Buy Clay. Buy a chatbot. Turn on automation. Expect pipeline to appear.

Neither works.

The teams seeing results are rethinking how buyers actually buy and then redesigning their systems around that reality.

HOW SENDOSO REBUILT OUTBOUND WITH AI

One of the biggest shifts Sendoso made was moving outbound under marketing and treating it like a data orchestration problem instead of a pure people problem.

What used to be a very manual, human-led SDR process is now AI-assisted from end to end. Tools like Clay are used to orchestrate data across job changes, intent signals, CRM history, and ICP context.

AI is not blasting generic emails. It is generating custom sentences based on real inputs. Not fake personalization. Actual relevance.

Humans are no longer spending their days stitching lists together or swapping variables. They are focused on strategy, messaging quality, and multi-channel execution.

That distinction matters.

WHY MULTI-CHANNEL IS THE BASELINE NOW

Email alone is not enough anymore. Kris was very direct about that.

What works is coordinated effort across channels. Email, phone, LinkedIn, direct mail, ads, and events all reinforcing each other.

AI helps make this scalable, but effort still matters. Teams trying one or two channels struggle. Teams that orchestrate multiple channels consistently break through.

AI reduces friction. It does not remove the need for thoughtful execution.

USING AI FOR INBOUND AND NURTURE

On the inbound side, Sendoso uses AI to qualify demo requests, route leads more intelligently, and nurture high-intent visitors who do not convert right away.

This is not about replacing reps. It is about removing delays and wasted motion.

The result is cleaner handoffs, better segmentation, and more productive use of sales time.

WHAT ACTUALLY HAPPENED TO THE SDR ROLE

This is the part most founders get wrong.

Sendoso did not eliminate SDRs. They changed the role.

A multi-person inbound SDR team was reallocated. AI now handles repetitive qualification work. Humans focus on targeted ABM outreach, account strategy, and creative execution.

The SDR role is becoming more technical, more senior, and more valuable. One strong SDR using modern tools can produce what five to ten legacy SDRs used to.

This is not job loss. It is job evolution.

WHERE HUMANS STILL MATTER MOST

Kris was very clear that AI does not replace relationships.

Cold calls. Executive conversations. Events. Enterprise deals. These still require humans.

In fact, as AI increases noise, human connection becomes more valuable, not less.

The best reps I see are not afraid of AI. They are learning it fast and using it to amplify their judgment and creativity.

WHY DIRECT MAIL STILL WORKS

One of Sendoso’s strongest channels is still direct mail and gifting.

AI makes it easier to pick the right accounts, personalize messaging, and automate logistics. But the real advantage is contrast.

Everyone gets dozens of cold emails a day. Almost no one gets a thoughtful package at their door.

Direct mail works because it is intentional and hard to saturate. When paired with AI-driven targeting, it becomes a serious pattern disruptor.

WHAT THIS MEANS FOR FOUNDERS

Here is the big takeaway.

Buying AI tools is not a GTM strategy.

Modern go-to-market requires system design. You have to decide what gets automated, what stays human, and how the pieces fit together.

This is why founders who think clearly about GTM early tend to win. And it is why companies that try to bolt AI onto broken systems keep struggling.

FAQ

Q: Will AI replace sales teams?
A: No. AI replaces low-leverage tasks. It raises the bar for what great sales teams look like.

Q: Should early-stage founders invest in AI GTM tools?
A: Yes, but only after defining ICP, buyer journey, and core workflows.

Q: Is outbound still effective?
A: Yes, but only when it is multi-channel and personalized.

Q: What skills matter most for reps going forward?
A: Relationship building, AI fluency, judgment, creativity, and systems thinking.

CTA

If you are a founder or revenue leader and you know your go-to-market motion is outdated, the answer is not another legacy sales framework or generic training program.

At Higher Levels, we work directly with founders and leadership teams to design and implement modern GTM systems that combine AI with real human execution.

If you want help doing this the right way, you can learn more about our consulting work here: https://www.higherlevels.com/contact-us

TL;DR

  • AI does not replace sales teams. It changes what good looks like
  • Old GTM playbooks are breaking and AI alone is not the answer
  • Winning companies rebuild GTM as systems, not tool stacks
  • Humans still matter where judgment and relationships count
  • Founders need implementation support, not outdated training

DATE LAST UPDATED

January 2026

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