framework · account-based outreach · 2025 build

Account-Based Outreach: a step-by-step guide for Midmarket and Enterprise Sales Teams in 2025

In this guide, I’ll share a framework for engaging midmarket and enterprise accounts during the dark times of quasi-personalized AI-generated clutter and sellers struggling to grab the eyeballs of decision makers.

author Dan Gridin · 15+ years in enterprise outreach, US to Mongolia

scope 30+ niches, non-SaaS friendly — software development, industrial equipment, you name it

target upper-midmarket and enterprise accounts · not for SMB math

tech stack basic LLMs + a little bit of Clay. Processes > bells and whistles

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• Account-Based Outreach: a step-by-step guide for Midmarket and Enterprise Sales Teams in 2025
• Four steps of engaging an enterprise account with cold outreach
• 1. Assessment
• Blocks of the assessment model
• Account Assessment: How to leverage AI
• 2. Preliminary Account Research
• Five steps of the preliminary account research
• Step 1. Grasp the big picture of what’s going on in the account's industry
• Step 2. Understand the key initiatives of the account
• Account Research: how to leverage AI
• Step 3. Deep-dive into the initiatives that can be tied to your offer
• Step 4. Draft the account map
• Step 5. Research the potential stakeholders
• Account research results
• 3. Account-specific value hypotheses
• Six-step framework for creating a value hypothesis
• Result - 5-7 value hypotheses per target account
• 4. Outreach cadences
• Building blocks of the first message
• Crafting the cadence
• Epilogue. Labor costs.
• Key takeaways and next steps
• Project artifacts
• Tangible results of implementing the framework
• Next steps

This approach rests on the 15+ years track record in helping enterprise teams from the US to Mongolia in 30+ niches. So even if you work in a non-SASS company and, for example, sell software development or industrial equipment, this framework will get you covered.

Now let’s set the mood with a 22-second video (old meme, but still pure gold) … and dive in.

the map

Four steps of engaging an enterprise account with cold outreach

These are the key building blocks that we’ll cover in this framework.

Let’s talk about every step in exhaustive detail.

step 01 / 04

1. Assessment

If you send cookie-cutter cadences with minor personalization, one or two “bad apples” in the account list is not painful. But in the situation when prep. work for every target account takes (spoiler alert!) 30+ hours of the team, the mistakes in account selection can be really painful and demotivating.

This is where the assessment model comes into play.

Blocks of the assessment model

step 02 / 04

2. Preliminary Account Research

At this stage, we need to gain enough account intel to start highly personalized convos with various stakeholders across the account.

It’s easy to get carried away with a variety of data sources, so I strongly recommend you use the “top-down” framework and slowly move from generic intel sources (10 Ks, investor calls, etc.) to contact-specific digital traces (interviews, LI posts, etc.).

Here’s a reference table with the typical intel sources.

Five steps of the preliminary account research

Step 1. Grasp the big picture of what’s going on in the account's industry

You need to feel the zeitgeist: what are the major market shifts, what the leaders are doing etc. Then, understand how your target account is coping with those changes.

Step 2. Understand the key initiatives of the account

It's extremely hard to land a large deal if it's not somehow attached to a strategic initiative.

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Account Research: how to leverage AI

This is the part where AI tools really shine.

With proper prompting techniques, you can analyze incredible volumes of various data sources (websites, PDFs, YouTube videos, etc.) for a mere fraction of the time compared to the age of manual labor.

My go-to tool at this stage is NotebookLM by Google:

A word of warning — although there are quite a few platforms that claim to conduct a “done for you” account research, their output is usually severely worse compared to NotebookLM or Chat-GPT.

Here’s a 12-minute video that proves my point

Step 3. Deep-dive into the initiatives that can be tied to your offer

Now let's take a closer look at the important projects inside the account that could benefit from your offerings

Step 4. Draft the account map

Now let's get a glance at the potential members of the decision-making unit (DMU).

Step 5. Research the potential stakeholders

Let's uncover some insights that will help engage with the buying group members (I prefer to start low and get some additional intel before reaching out to the C-Suite).

Account research results

The main artifact of the PAR stage is a spreadsheet with intel nuggets, that are described in the following fashion:

1. Hypothesis a.k.a. insight — what account-related event can be used as an outreach trigger
2. The reason why — what are the triggers that make us think the offer can be relevant
3. Reference — link to the source that contains the intel nugget.

Here’s how the final doc can look like:

step 03 / 04

3. Account-specific value hypotheses

In the previous steps, you gathered a lot of scattered insights. Now it’s time to assemble them into super-personalized takes for different business units inside the target account.

In an ultimate must-read, A Practitioner's Guide to Account-Based Marketing, Bev Burgess shared a very elegant visualization of the difference between segment-based and account-based value props:

To create a value hypothesis, I would recommend using a six-step framework (again, taken almost verbatim from Bev’s wonderful book)

Six-step framework for creating a value hypothesis

Result - 5-7 value hypotheses per target account

Here’s an example of what a structured value hypothesis can look like (please keep in mind that during this stage you need to draft several of those hypotheses for different business units as it will maximize your chances of hitting the target).

step 04 / 04

4. Outreach cadences

Building blocks of the first message

Here’s the typical structure of a first message created and made famous by the Lavender Crew.

1. Trigger based on account intel nugget
2. Assumption based on the trigger
3. Elevator pitch of the value hypothesis
4. Soft CTA (a.k.a. never ask for the call in the first message)

A well-executed research should allow you to easily craft a unique "take" for each potential stakeholder in the target account.

In other words, we are not trying to create an “ultimate outreach” that will blow Mr. Big Decision Maker’s mind. Instead, we launch dozens of highly personalized cadences across the account.

I often call this approach “Death by a thousand cuts” (凌遲). It may sound harsh, but that’s exactly what we are doing here.

Crafting the cadence

Given the intense (almost insane) amount of “targets” inside one account, I would recommend going rather easy with the cadences themselves — stick with 7-8 touches both in email and LI across 10 days.

A few random thoughts:

• The first message will generate at least 50% of all the responses
• The best cadence frameworks are useless without a research-driven value hypothesis
• Use the “working bees first” approach – launch cadences to the bottom and then enrich your C-Level outreach with the insights received from the lower levels.

And don’t forget that It’s impossible to create an engaging message without the intel nugget. No amount of generic wordsmithery will engage the C-Level exec. So first you need a solid data-driven hypotheses and then “package it” into digestible cadences.

epilogue

Epilogue. Labor costs.

Now to the really sad part. All these bespoke, fully personalized cadences will cost ya’.

In last year's build of the framework, I mourned over the fact that the account-based approach to cold outreach might be unusable by most sales teams due to the extreme amount of labor required for research.

But the AI revolution equipped sellers with the tools that can speed up data extraction by at least ten times and thus severely lowered the entry threshold.

However, I still can’t recommend the framework to the folks closing $5K deals, cause you still need to relocate significant brainpower to craft uberpersonalized multi-stakeholder takes for every target account.

So here is a detailed video walkthrough of the spreadsheet (btw, here’s the source file).

And that sums up the lead generation framework that will allow you to engage almost any tier-1 account.

takeaways

Key takeaways and next steps

Next steps

I guide sales and marketing teams to routinely engage tier-1 accounts around the globe and win the biggest enterprise deals faster with less dependency on the “human factor”. Ping me on LinkedIn or drop a line at dan@dangridin.com