What I’m Chasing in 2026
I’m trying a new format for this newsletter. Reply if you like it (or don’t).
Let’s dive in.
The Briefing
Stories and news from the last month
1. Lovable Raises $330M to "Kill SaaS"
My take: The first billion-dollar company run by a team of <5 people is coming in 2026. For sales - if AI can upgrade your product in 10 hours, your 60-day sales cycle built on "features and roadmap" is dead. The only thing left to sell is outcomes, speed, and risk reduction.
2. When to Leave After a Quota Change
My take: If your company changes your comp plan WITHOUT changing your role, they're fixing THEIR budget problem on YOUR back. The tell? Look at team attainment — if nobody's hitting quota, it's not a performance problem, it's a leadership problem.
3. Salesforce Doubles Down on AI SDRs
My take: Salesforce is betting the future of SDR work is AI agents handling inbound qualification. If your SDRs are still asking "what brings you to our site?" on chat, they're doing work that's worth $0 in 2026. The BDR role isn't dead—but the BDR who only knows how to work sequences and answer chats is.
The Year Ahead
This year I’m going back to a routine that’s worked in the past — writing 3 accomplishments at the end of every day. I stole this from The Gap and The Gain. It keeps me accountable and highlights actual progress.
Alright, onto some goals for 2026:
5. Play Six Rounds of “Business Golf”
This one is straightforward. Golf is my arena and a place where real conversations happen—no agendas, no slides, just four hours to see how someone actually thinks.
This includes rounds with partners and clients during travels, combined with networking opportunities or hosting at my club. Last year I played three rounds of business golf - this year I’m doubling it.
Let me know if you’re interested
4. Mentor Two People Breaking Into Tech Sales
I've had a lot of people reach out asking for career advice over the years. Most of the time it's a quick call and that's it. This year I'm committing to help 2 people make the jump.
If you're early in your career or trying to break into tech sales or take the next step in your career, shoot me an email in Q1.
3. Drive $1M in Revenue
This combines two tracks: building the partnership program at my W2 job and helping early-stage companies through consulting. The W2 quota covers the majority—building pipeline, closing partner deals, and proving the channel works at scale. The consulting work focuses on: building sales programs for start-ups, developing partner channels, and rep development.
Both count toward the $1M (more on consulting opportunities in the P.S. below).
2. Join the 5AM Club
I've been waking up between 6:30-7:30. It's fine. But I feel like some days I’m lacking routine and leaving time on the table. Next year I’m waking up in the 5 o’clock hour for at least 150 days. A simple breakdown to explain why:
Waking up 1 hour earlier each day → 5 hours per week.
5 hours per week * 4 weeks → 20 hours per month
20 hours per month * 12 months → 240 hours per year
144 hours per year → 20 full days
Great book for those interested
1. Build ‘The Partnership Playbook’
In November I shared the - 2026 Outbound Playbook.This year I'm building The Partnership Playbook—a tactical guide for early stage companies looking to build new revenue channels.
As of this sending, I've mapped out the structure, frameworks, and partner qualification system. With any luck, it will be completed this summer. More to come.
Reddit Post of the Week:
Sales has always been "justify your worth or start interviewing"
From the Reddit archives
Hottest Email Template of 2026:
Now this is one way to stand out in inboxes.
Please don’t do this
The Best Thing I Heard This Week:
Stop selling what your product does - start selling who your customer becomes.
P.S. Consulting Offer
Last year I helped three Series A+ companies accelerate sales growth.
Common problems they had:
Scaling from founder-led sales to predictable revenue
Growing outbound sales and rep development
Building a partner channel from the ground up
If you're interested, hit reply and let's talk.
Chris is a Director of Sales
Until next Thursday,
TSG
P.S. I reply to all emails.