AI Strategist · Sales Leader · Builder

The Sales Leader
Who Builds AI.

20 years scaling SaaS teams to $415M+ in revenue. Co-founded an ML company (acquired). Now I build the AI tools and strategies that give revenue teams a structural competitive advantage.

Organizations I've Scaled

GrouponDocuSignCloudKitchensProkeepCareerBuilderSpringCM
About

From Scaling Sales Teams
to Scaling Intelligence

I've spent two decades building SaaS revenue organizations — from zero to 400+ sellers, from first dollar to $415M+, at companies like Groupon, DocuSign, and CloudKitchens.

But here's what makes my background different: I didn't just discover AI last year. In 2013, I co-founded SimpleRelevance, a machine-learning SaaS platform that sold predictive analytics to Fortune 500 clients in Financial Services, Media, and Retail. We were acquired by Rise Interactive in 2015. I've been building at the intersection of AI and revenue since before it was a buzzword.

Today, I combine that deep operating experience with hands-on AI development. I build autonomous agents, AI-powered prospecting systems, and intelligent forecasting tools — not as demos, but as working systems that give revenue teams a real competitive edge.

Whether you're a startup trying to find product-market fit or an enterprise looking to transform your GTM motion, I bring something rare: a leader who has scaled massive sales organizations AND who builds the technology to make them better.

$415M+
Revenue Generated
400+
Sellers Scaled & Led
20+
Years in SaaS Sales
Average Pipeline Growth
Services

How I Help

AI-Powered GTM Strategy

I design go-to-market strategies that leverage AI for smarter prospecting, personalized outreach, pipeline forecasting, and deal intelligence. Not theory — executable playbooks your team can run tomorrow.

Sales Organization Design & Leadership

From building your first sales team to restructuring a 400-person org, I bring the operating system: hiring profiles, comp plans, territory design, enablement programs, and performance management frameworks.

Fractional / Advisory Sales Leadership

Need a senior sales leader without the full-time commitment? I serve as a fractional CRO/VP Sales or board-level advisor to help you hit your next growth milestone.

How We Work Together

Three ways to engage, depending on what you need and where you are.

1–2 weeks

Advisory Sprint

Rapid assessment and strategic recommendation. Ideal for GTM audits, AI readiness evaluations, or a senior second opinion on a major sales decision.

Deliverable
Written strategy brief + 2 working sessions
Ideal for
Companies facing a specific, defined challenge
3–6 months

Fractional Leadership

I embed with your team part-time as a fractional CRO or VP Sales. I attend pipeline reviews, coach your managers, and build the systems that scale.

Deliverable
Ongoing operational leadership + weekly engagement
Ideal for
Series A–C companies scaling past $5M ARR
Custom

AI Revenue Transformation

End-to-end design and deployment of AI-powered sales systems — from agent builds to workflow automation to team enablement. I build the tools, train the team, measure the results.

Deliverable
Custom scope: tools, training, and measurable outcomes
Ideal for
Organizations ready to make AI a competitive advantage

Investment varies by scope and engagement type. Let's talk about fit →

Free Resource

Get the Playbook

7 AI workflows that are changing how top sales teams operate. Specific, actionable, and ready to implement this week. Free.

  • Account research in 30 seconds
  • AI-powered deal coaching
  • Autonomous outbound sequencing
  • Forecast signal scoring
  • Win/loss pattern extraction
  • GTM blueprint generation
  • Champion tracking & alerts
Free Resource
The AI-Powered Sales Playbook
7 Workflows You Can Implement This Week
Sent to your inbox·Free forever

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Experience

The Track
Record

Two decades of building. Now available to build for you.

Case Western Reserve University
BA Political Science · Cum Laude
Get in touch →
Prokeep
Senior Director of Sales
Nov 2024 – Nov 2025
GTM strategy driving 30% of company revenue · 3× pipeline expansion · 3 new verticals
CloudKitchens
Head of Sales, Central U.S.
Nov 2022 – Dec 2023
4 regional teams · 15 markets · tens of millions in annual revenue · 300% increase in outbound demos
DocuSign
AVP & RVP of Sales
Jan 2019 – Sept 2022
70+ AEs · quota in the tens of millions · significant net new ARR · Multi-product adoption 8% → 41%
SpringCM → DocuSign
VP Business Development
Feb 2018 – Sept 2022
Founded BD org, $1.5M new revenue in 6 months · Executive sponsor on $10M+ ACV deals
SimpleRelevanceCo-Founded
Co-Founder & VP
Jan 2013 – Dec 2016
Built ML/predictive analytics SaaS for Fortune 500 clients · Acquired by Rise Interactive
Groupon
Regional Vice President
Aug 2010 – Sept 2012
0 to 400+ sellers · $415M+ revenue · 23 new markets · Consumer Goods at $8M/mo run rate
CareerBuilder
Sales Director
2004 – 2010
Built SMB team from 0 to 240 sellers · tens of millions in division revenue
Contact

Let's Talk

Whether you're looking to hire a sales leader, need help building your AI strategy, or want to collaborate — I'd love to connect.

Q2 2026 availability: Limited. Reach out early.
Email
joe@joepeck.ai
Website
joepeck.ai
LinkedIn
joseph-p-peck
Schedule a call
Book 30 min →
Typical response time
Within 24 hours
I read every message personally.

I read every message personally and respond within 24 hours.