| ISSUE №188 · AGENCY SALES | LEAD GENERATION |
It’s A Bit Of A Bittersweet Time Of Year
My youngest kids went back to school last week. They (twins) are 17, and I’m not sure that college is in the cards for them, but every fall that passes reminds me that they are a step closer to being ready to take flight.
The end of the MLB season is racing towards us which means my favorite TV show is going to end soon enough. Luckily, it seems my beloved Red Sox are headed to the post-season, which means I’ll get at least a couple of bonus episodes.
Summer, in New England, hands off to fall pretty quickly. Hot, humid days turn into cool, crisp nights and the sun sets earlier and earlier. It just reminds me that those evening trips to walk on the beach are going to go into hibernation soon enough.
It makes me a little wistful and I want to reminisce.
But A Quick Look At My 2026 Annual Plan Reminds Me That There Is A Lot Of Work To Do This Year
…and as the bittersweet of summer into fall reminds me, THERE AIN’T THAT MANY DAYS LEFT IN 2026 TO GET ALL THE STUFF DONE THAT I SET OUT TO DO! As of this post, there are 74 business days left in 2026. There’s actually, probably fewer. If you take out the week of Thanksgiving, the week of Christmas, and the week before New Year's, there are actually only 60 business days left in 2026. How are we going to use the days the most effectively?
Scenario #1 - You’ve Got Folks In Your Pipeline But Nobody Is “Hot”:
This is a pretty regular scenario as people return from the summer doldrums. The very first thing that you need to do is immediately understand where they are in the realm of possibility:
Inbound or Referral: Those deals close usually 2.5 to 3 times the rate of someone you put into your pipeline. If you normally close 20% of opportunities you sourced, you have a 50-60% chance of closing an inbound or referral opportunity. In some ways, these are fish in a barrel, & you have got to start shooting. Based on everything you know, what is their primary need? Why did they reach out to you, or why were they referred to you? If you don't have that information right now, go get it. Find the strongest connection point between what you perceive their need to be, and your service. Start making a business case where the benefit is as front-loaded as possible so that this prospect gets as much benefit as they can this year. If you aren't in active conversations, craft an email right now saying, "Hey, I was thinking about [something in their business that connects to that strongest need/service connection point]. I’ve got some thoughts on how we might be able to make real progress in solving this before the end of the year. Can we meet before the end of the week - I want to make sure that we have time to plan this out well so you get the biggest bang for your buck. I’m open Thursday afternoon - does that work for you?”
The magic here is two sided:
a) You need to have a real sense of what their big issue is & what downside they will experience w/o an immediate fix.
b) You should have a plan that yields measurable results ASAP.
If you can articulate both of those, and you lean heavily on the trust based on the referral and/or the fact that they already liked you enough to bring you into the discussion, you have a terrific opportunity to close a deal this month.Outreach Driven Pipeline: Outreach driven pipeline typically isn't as close to a buying decision as inbounds or referrals, so you've got to do some more work.
If you aren't in active conversations with them. I want you to deliver them some value right now. Get your favorite LLM fired up, look at Q4, growth patterns, opportunities, or threats for similar clients you have worked with in the past, and start throwing prior performance data, market research and everything you can scare up about the prospect, and craft an email that says something like “Hey, I know we haven’t had our intro call yet, but I wanted to share some research with you based on everything we're seeing in the market. In Q4 last year, our clients who are similar to you experienced [good things or bad things]. Based on some research we’ve done, we think [good thing or bad thing] is going to be [better or worse] because of [market trend, research or content from neutral 3rd party]. Based on what I know about your business, we are sure that we can [amplify good thing or mitigate bad thing] - but time is of the essence. We want to make sure that we are up an running ASAP - Q4 starts in a little over 2 weeks. Do you have time tomorrow?”
How Jennifer Aniston’s LolaVie brand grew sales 40% with CTV ads
For its first CTV campaign, Jennifer Aniston’s DTC haircare brand LolaVie had a few non-negotiables. The campaign had to be simple. It had to demonstrate measurable impact. And it had to be full-funnel.
LolaVie used Roku Ads Manager to test and optimize creatives — reaching millions of potential customers at all stages of their purchase journeys. Roku Ads Manager helped the brand convey LolaVie’s playful voice while helping drive omnichannel sales across both ecommerce and retail touchpoints.
The campaign included an Action Ad overlay that let viewers shop directly from their TVs by clicking OK on their Roku remote. This guided them to the website to buy LolaVie products.
Discover how Roku Ads Manager helped LolaVie drive big sales and customer growth with self-serve TV ads.
The DTC beauty category is crowded. To break through, Jennifer Aniston’s brand LolaVie, worked with Roku Ads Manager to easily set up, test, and optimize CTV ad creatives. The campaign helped drive a big lift in sales and customer growth, helping LolaVie break through in the crowded beauty category.
Scenario #2 - You’ve Got Folks In Your Pipeline But They Just Can’t Decide:
This is a completely regular and normal thing. As we've discussed before in this newsletter, your solution only represents a small portion of the totality of your client's business. Whatever the issues you solve may not be the ones that are the most on fire right now, so they may not be ready.
Regardless if they are putting out other fires or just dragging their feet, I want you to craft an email right now that says:
Option 1 - Closing Window: “Hey, I know that we have an offer outstanding. We just want to make sure that we get you in on time so that we can execute as well as possible in Q4. As we’ve discussed, we expect that you can generate [clear, measurable results].
We’ve been looking at the calendar, and have got to get our onboarding scheduling handled and our staffing plan solidified. I’d love to get our agreement signed and done before [date 10 days from now]. We can adjust the effective date of the contract so that it starts the day onboarding starts, if that helps, but I want to make sure that we have your onboarding locked in so we don’t miss out on [clear measurable results].Option 2 - Just A Test: “Hey, I know that we have an offer outstanding, but we haven’t been able to get to a decision yet - we’ve put together a sprint version of our offer and I’d love to see if you’d be interested. It’s [number of weeks long] and encompasses [parts of your larger offer], and is less expensive. Think of it as a way to work with us without making a long term commitment right away. I’m open on Thursday afternoon.”
Some teams never seem to stop moving. They're on Attio, the agentic CRM.
It’s your always-on revenue engine: agents and workflows build pipeline, chase every buying signal, and move deals forward alongside your team.
Teams like Parallel, Turbopuffer, and Wordsmith build on Attio. Are you one of them?
Scenario #3 - Pipeline Is Empty:
OK, so this means that we are in panic mode. There are 4 plays that I want you to make right now.
Account Growth: Look at every current account that isn’t UNHAPPY with you and come up with 3-5 ways that you could help them grow by the end of the year. Get a meeting with the your everyday POC and the most senior person on the other side and make a pitch for them to spend more this year because of the additional impact you see for them through the end of they year. (It doesn’t even have to be an ongoing thing into 2027…)
Everybody Who Said No To You In The Last 12 Months: Obviously, you don't know if they are happy or if they've solved their problem, but for every single opportunity that you made a pitch to that did not choose you, look at whatever you can from the outside & ask if all of their problems that you spoke about have been solved. If they haven't, offer up some free consulting and restart the sales process. Likely the deal will be a little smaller than the first one might have been, but if there's nobody in your pipeline, beggars can't be choosers.
Everybody Who Churned In The Last 24 Months: Similar to the play above, unless it was acrimonious, reach out to everyone that you used to work with. The fundamental approach is look at whatever you can from the outside & ask the status of the problems worked on together have been fully solved. If they haven't, or if another set of growth issues has come up, use the same free consulting concept and see if there is an opening to restart the engagement or if there's an opportunity to offer them a sprint, like in scenario #2.
Super-Targeted Outreach: this play demands that you have a tight ICP, the ability to build a short target list, and you’ve got some recorded sales and client calls and access to the LLM of your choice. Below is a generalized .skill file that you can riff on and an example of an outreach brief that kicks some ass.
Here’s the play:
a) Mine your sales and client calls for specific market needs. Come up with outreach themes and angels.
b) Do deep research on your target list (10-15 targets at a time). Look for things on their site, podcasts they’ve been on, news stories about them, market data….any thing that might give you an angle of approach.
c) Match brands and angles and get emailing/DMing
I want to give you an idea of what the brief might look like, and a skill that you can start with so you aren’t all “Thanks, Tim, 4a - 4c is useless…”:
The Future of AI in Marketing. Your Shortcut to Smarter, Faster Marketing.

This guide distills 10 AI strategies from industry leaders that are transforming marketing.
Learn how HubSpot's engineering team achieved 15-20% productivity gains with AI
Learn how AI-driven emails achieved 94% higher conversion rates
Discover 7 ways to enhance your marketing strategy with AI.
The Brief
The Skill
---
name: outreach-themes
description: Turn sales and client call transcripts into an outbound working brief. Extracts the recurring themes buyers actually talk about, writes a one-paragraph thesis, picks a benchmark brand that proves the thesis, builds outreach angles for a target list of named brands, and maps every brand to the theme that fits it best. Use this whenever someone has call recordings, transcripts, discovery notes, or customer interviews and wants outreach angles, account-based messaging, a target-list brief, "what should we say to these accounts," "find the themes in these calls," "build a brand-by-theme map," or "turn these calls into outbound." Use it even when they only paste transcripts and a list of company names and say "do the thing."
---
# Outreach Themes
Buyers tell you what they want in calls. Then everyone goes and writes cold email about something else. This skill closes that gap. Calls go in, a working brief comes out: thesis, themes, benchmark, angles, and a brand-by-theme map the team can actually work from.
## Inputs you need
1. **Transcripts.** Sales calls, discovery calls, client check-ins, customer interviews. Three is a floor. Eight to fifteen is where patterns get honest.
2. **A target list.** Named brands or companies the user wants to reach. Five to twenty-five works. If they give you fifty, ask which fifteen matter most.
3. **What the sender sells.** One or two sentences. If it's missing, infer it from the transcripts and state your inference at the top of the brief so it can be corrected.
If any of the three is missing, ask once, then proceed with what you have and label the gaps.
## The process
### Step 1: Mine the transcripts
Read every transcript fully before writing anything. On the first pass, pull out every moment where a buyer:
- names a problem in their own words
- describes what they tried that didn't work
- explains what success would look like
- reveals a belief about their customer or market
- pushes back on the seller
Keep the buyer's language. "We keep acquiring people who churn at month two" is a theme. "Retention challenges" is a category label and it's useless for outreach.
Then cluster. A theme is a pattern that shows up in at least two calls from different buyers. One buyer's pet peeve is an anecdote, not a theme. Aim for three to five themes. Four is the sweet spot. Six means two of them are the same thing wearing different hats.
For each theme, capture:
- **Name** (two to five words, in the buyer's register, not the seller's)
- **The buyer quote** that best carries it (verbatim, anonymized)
- **The mistake** most brands make about it
- **The counter-move** the sender offers
Read `references/theme-extraction.md` when the transcripts are long, messy, or the themes are refusing to separate.
### Step 2: Write the thesis
One paragraph. Four to six sentences. It names the thing every brand on the list is getting wrong and states the reframe. The test: a stranger on the target list should read it and feel slightly caught.
A thesis is not a value proposition. "We help subscription brands grow" is a value proposition. "Growth is recruiting strangers, and subscription was built for believers" is a thesis. The thesis makes the themes cohere. If a theme doesn't hang off the thesis, either the thesis is too narrow or the theme belongs in a different brief.
Highlight the single sentence that would work as the first line of a cold email. That sentence gets reused everywhere.
### Step 3: Pick the benchmark
Choose one brand (from the target list or from the wider market) that visibly does the thesis right. It becomes the comparison point in every angle: "IM8 does X. You're doing Y." The benchmark should be a brand the targets already respect or envy. Nobody wants to be told they're worse than a company they've never heard of.
Write a short benchmark section: what they do, why it proves the thesis, and one or two observable details (a landing page move, a pricing structure, a retention mechanic) that a target can go verify in five minutes.
If no brand on the list qualifies, say so and pick one from outside it. If the user names one, use theirs.
### Step 4: Build the brand-by-theme map
This is the core artifact. Every brand on the target list gets one row. Every row has:
| Column | What goes in it |
|---|---|
| Brand | Name, category, rough size if known |
| Primary theme | The one theme that fits this brand best. One, not two. |
| Secondary theme | Optional. Only if it's a real second fit. |
| Evidence | One observable fact that makes the theme fit. Something from their site, their ads, their pricing, their reviews, a news item. Not a guess. |
| Angle | One or two sentences. What you'd say to this brand, in this theme, against the benchmark. |
| Opener | The first line of the outreach, written out. |
Research each brand before assigning a theme. A theme assigned without evidence is a guess and the reader will know. If web access is available, check the brand's homepage, pricing page, and any recent press. If it isn't, say the row is unverified.
Cap themes at roughly even distribution. If eleven of twelve brands land on the same theme, the themes are wrong, not the brands.
### Step 5: Write the angles
For each theme, write one reusable angle block:
- **Who this is for** (what kind of brand on the list)
- **The observation** (what you noticed about them, template form with a slot for the evidence)
- **The reframe** (the thesis applied to their situation, one line)
- **The benchmark contrast** (what the benchmark does instead)
- **The ask** (one specific next step, small)
The per-brand opener in the map is this block collapsed to one sentence with the evidence filled in.
### Step 6: Account facts
Close the brief with a facts sheet for the target list: founded, estimated revenue, model (subscription, retail, D2C, hybrid), platform if visible, funding if known, anything you saw that would change the angle. Mark every unverified item. This section exists so the person doing outreach doesn't have to re-research.
## Output format
Deliver a single working brief with these sections, in this order:
1. **Header**: sender name, "Outbound Working Brief," and a headline that is the thesis compressed to five to eight words in all caps
2. **The Thesis**
3. **The Themes** (three to five, each with name, buyer quote, mistake, counter-move)
4. **The Benchmark**
5. **Brand × Theme Map** (the table)
6. **Angles** (one block per theme)
7. **Account Facts**
Default to a designed HTML page if the environment can render one, otherwise Markdown. See `references/brief-format.md` for the layout and the writing rules that keep this from reading like a consultant's deck.
## Writing rules
- Buyer language beats category language every time.
- No em dashes. Commas or parentheses.
- Every sentence has a subject and a verb.
- Do not announce a point before making it. No "Here's the thing." Just say the thing.
- Contractions are fine. Hedging is not. If you don't know, mark it unverified and move on.
- Angles are sharp, not rude. The reader should feel seen, not insulted.
## What good looks like
The brief passes when a salesperson who never heard the calls can pick any brand on the map, read the row, and send a credible first email in under ten minutes. If they'd still need to go research the brand or figure out what to say, the map isn't done.
Need Help Getting That Pipeline Filled?
Book a call. It’s free. I swear to gawd that I will make you laugh, and I am almost 100% sure that together, we can solve your problem.






