Welcome to Hacking SaaS Sales

Use AI to craft winning business POVs that increase AOV in 6 months (or less).

Who is this for?

• Founders who want to sell better, know their product better than anyone, but don’t have a sales background.

• AE’s who struggle to craft POV’s that resonate with enterprise, mid market, or SMB buyers.

• SDR’s who don’t know how to craft POV’s that are tailored towards their target prospect personas.

Crafting a clear business POV can be time consuming.

Lacking a winning business POV ends up in outcomes like longer sales cycles, not resonating with prospects and buyers, or worse, pressing “close lost”.

A well-crafted business POV—combined with AI-driven insights—is the key to winning deals and increasing average order values.

Inside of Hacking SaaS Sales, I’ll show you frameworks and processes that help you to use AI, craft winning POV’s, increase AOV’s, and sell more — every Saturday.

You’ll also get access to SaaS Market Trends, so you’re always in the know on what’s happening in the SaaS industry.

Who am I?

Hacking SaaS Sales is written by me, Andrew Kobylarz.

I’ve spent over a decade in enterprise SaaS sales, working at series A/B startups and closed over $15mm in SaaS contracts. I’ve sold to marketing, insights/analytics, and developer personas, helping startups land and expand within Fortune 500 companies.

Best Issues

Still not sure if Hacking SaaS Sales is for you?

Here’s some of my most read issues:

Crafting Your Business Point of View

• Learn to Read Your Customer’s Mind: Building a Business Hypothesis/Point of View For Your Customers with AI

• Stop Making Your Prospects Think: Putting Your POV/Hypothesis into Action

• How To: Finding the “Right” Customers

• Beyond Email: Using Texts to Deepen Client Trust (Key Questions to Strengthen Your Sales Relationships)

SaaS Sales Market Trends

• GTM is Changing: Are you Ready?

• 6 Ground Level Tactics You Need: Easy Tips You Can Apply Today

• How AI Agents are Coming for Your Job (And How to Stay Ahead)

Break into Tech Sales

• How to Land a SaaS Job in 60 Days (part I,II, and III)

• The Hidden Trap of OTE

And yes - when you subscribe you get access to the entire archive of Hacking SaaS Sales (free courses and over 1.5 years of content).

My Promise to You

• I’ll never miss a week: Every Saturday you’ll get one email covering SaaS sales market trends and/or frameworks on SaaS sales using AI. All helping you to craft winning POV’s and increase your AOV.

• I’ll never stop innovating: I firmly believe that AI isn’t going to “replace” sales. But it will 10x a seller’s output. And the cornerstone of doing that is having the ability to use AI to efficiently and effectively, craft a winning business POV. As the space evolves, I promise to share everything with I learn with you.

• I’ll iterate in real-time based on your feedback: If there are certain questions you have, problems you don’t know how to solve, or specific prompts you’d like me to create, just ask! I value you as a reader and always want to be creating what is most helpful for you and your goals.

As a reader, you can check for Hacking SaaS Sales here on Substack—or, sit back and wait for them to hit your inbox every Saturday.