I started my sales journey back in 2005. Every September, I update the list of empirics I live by (spoiler alert: none of them includes the word AI).
Here’s the updated list for 2024-2025.
Account research
- Almost any sales challenge can be unstuck with more research
- Always start enterprise account research with the latest earnings call transcribe.
- Always move top-down in your account research – start with the big picture and then focus on particular departments and stakeholders.
- Data easily obtained = data used by almost every seller. Dig deeper. Combine several data points to craft thought-provoking POVs
- Section 1A of the 10-K report (aka Risk Factors) is usually the most insightful
- Don’t use personal intel (hobbies etc.) in the cold outreach until it’s a slam dunk
- Study the career trajectory of the target exec before reaching out. This info can lead to some interesting assumptions.
- Nothing grabs attention better than a relevant research-based opener.
- Consider hiring a full-time junior analyst for relentless research on tier-1 accounts.
- Have the intel on every buying group member readily available for the selling team.
Outreach / Copywriting
- Master the Lingchi — death by 1000 cuts — lots of solid hypotheses delivered to different stakeholders
- "Creative" outreach with snail mail, video, etc. is just a force multiplier. So if the offer is of 0 value — there’s nothing to multiply.
- Execs are reading emails (yours included) during other convos
- Boring unemotional research-based subject line (i.e. project x launch) beats the clickbaitish one any day of the week.
- Recapping is one of the most important skills for the enterprise seller.
- Saw a piece of copy you liked? Rewrite it by hand.
- Write drunk, edit sober (don’t be hard on the first draft, but be ruthless polishing it)
- Stop “clearing the throat” in your copy (no wordy intro paragraphs).
- More verbs, fewer adjectives.
- Always rewrite passive voice.
- BLUF (bottom-line up-front) — start with the main idea and then build the case
- Study the great copywriters of the past — Halbert, Carlton, Schwartz, etc.
- Every client story should include a pinch of imperfection (otherwise it’s unbelievable).
Working with the buying group
- Red flag. Champion badmouths your competition on the disco call
- Red flag. Champion doesn’t deliver on small commitments.
- Red flag. Champion is super excited about your offer with zero skepticism.
- In a buying group of 7 people or more, at least 2 people hate each other’s guts.
- The more the buying group, the more it leans towards risk reversal.
- Red flag. Smooth sales process with zero hard questions along the way. There probably is a crisis you are fully ignorant of.
Megadeal mindset
- Deal with a big account under the sign-off level of C-1 exec is not enterprise selling.
- If you want 6-figure deals — work with existing demand. If you want 7-figures and above – create demand, and engage the C-Level up and early.
- Make your selling experience valuable for customers. Learn from McKinsey and other top consultants.
- There’s time for ego, and there’s time to be the dumbest person in the room.
Self-management
- Invest in therapy as early as you can.
- Concentrate on 2-3 things you are great at. Relentlessly delegate the rest.
- The first hour of every day belongs to your well-being.
- Learn how your body cycles work and build a workflow around them.
- Don't beat yourself up over the imperfections of your character - most probably your biggest breakthroughs in life were made possible thanks to them.
Like what you’ve just read? Great.
- Check out the infamous Account-Based Outreach for Enterprise Sales Teams framework
- Follow me on Linkedin
- Enroll in my upcoming enterprise outreach intensive (new cohort launches on Nov 4) or see how we can work together in other formats.