Head of Content @ LASSO | Co-host of That's Marketing, Baby | Delivering daily cheat codes for small content teams

I'm a creative director turned content marketer and strategist with more than 20 years of experience conceptualizing and executing breakthrough work for B2C brands like Eggo, Rice Krispies, Blue Cross, Cottonelle, and McDonald’s, and B2B brands like Fastly and Island.

I have a knack for leading cross-functional teams toward a common goal, bringing order to the oft-chaotic creative process, crafting insight-driven global campaigns, and bringing stories to life via long- and short-form content.

Jess Cook

I've worked with a lot of talented people over the years.
 
But every once in a while, you meet someone who just 𝘨𝘦𝘵𝘴 𝘪𝘵 in every way that matters.
 
Annalisa Rodriguez is one of those people.

I had the privilege of working with her for a short time at Fastly.
 
And this week, she joined Vector 👻 as our Sr. Content Marketer Manager — a sentence that makes me so happy I could cry.
 
Annalisa has a journalism background that shows in everything she touches. Long-form, repurposing, content design... she's equally amazing at all of it.
 
But what makes her truly special is her ability to take the things people 𝘴𝘢𝘺, turn them into content that makes readers 𝘧𝘦𝘦𝘭, and connect it all to results when buyers 𝘢𝘤𝘵.

(Read: not a common skill.)

Bonus: she's already vibing with us in Slack, and keeping our cat-loving hearts fed with pics and videos of her kitties, Oreo and Darkness. 😻
 
With Annalisa on the squad, we now have four marketers at Vector. And for the first time, a real three-legged stool:
 
→ Product marketing 
→ Demand gen 
→ Content

(i.e. I feel like I just collected ALL OF THE POKEMON.)

Annalisa's going to be sharing how she builds content here at Vector. You'll want a front-row seat for that, so go give her a follow.

Then stand back, 'cause sparks are 'bout to fly, y'all.

Just back from an incredible week at Above the Fold where I ran six content workshops over two days. I have but three pieces of photo evidence I was even there.

1) Schnitzel dinner with my ride or die agency guy, Justin Dunham. We've had two Zoom calls a week for nearly 5 years straight and had yet to meet in person. It was worth the wait. (For both the hang and the schnitzel.)

2) Got to meet my buddy from across the pond, Luke Winter - the man, the myth, the legend behind our "Next best way" ads. We talked shop (obvi), and concerts, and about what we do when we're not at our desks. His hair is just as fab in real life.

3) My parents were also flying out of Detroit at the same time as me - something we only realized a few days before. So we met up for an early bird special before boarding. They paid, of course, because I'm only 42. 🥰

So glad I went. So glad to be home. So ready for this damn snow to melt.

I have a rule I live by in marketing: Test small before executing big.

It's why I ran an influencer pilot before making it a full program.
Tested new messaging in ads before our repositioning launch.
And why I'm so excited about what we're announcing today...

Vector 👻 𝗶𝘀 𝗽𝗼𝘄𝗲𝗿𝗶𝗻𝗴 𝘁𝗵𝗲 𝗰𝗼𝗻𝘁𝗮𝗰𝘁-𝗹𝗲𝘃𝗲𝗹 𝗱𝗮𝘁𝗮 𝗯𝗲𝗵𝗶𝗻𝗱 𝗖𝗹𝗮𝘆 𝗔𝗱𝘀. 🎉 

Here's the metaphor that's been living in my head for this:

Clay is the proving ground. 🏁
It's where GTM teams experiment with signals, build enrichment workflows, test what actually predicts buying behavior, and figure out which audiences are worth activating.

Vector is the Autobahn. 🚗
Once you know what works? You open it up. Contact-level targeting, live audience updates, suppression logic that actually follows your buyers—running modern ads playbooks at full speed.

This isn't hypothetical for us.

It's exactly how Kelly and Sara have been building Vector’s ads program.

• Kelly uses Vector to identify accounts and contacts signaling intent. 
• Sara uses Clay to enrich and score those ICP contacts. 
• Then, they use Vector to activate those contacts across LinkedIn and Google, keeping our paid targeting aligned to real buyer signals as they move through the funnel.

When your team’s already living the use case, you know you're onto something.

Grab some time to see it in action: https://lnkd.in/eugn7rJh

I love a good Uno reverse. 

Especially when it's aimed at Joshua Perk 👻.

In the season two finale (!!!) of This Meeting Could've Been a Podcast, Josh and I take you through our entire website redesign process: from the awkward "you literally told me no when I suggested this six months ago" conversation (haha), to how we worked with our design agency to build the new look and feel, to the 37-item launch checklist 𝘴𝘰𝘮𝘦𝘰𝘯𝘦 (Josh) did not see coming.

But one of my favorite takeaways from the entire project goes a little something like this...

The second someone lands on your site, they start to form an opinion about your product. 𝗔𝗻 𝗼𝗽𝗶𝗻𝗶𝗼𝗻 𝘆𝗼𝘂𝗿 𝘄𝗲𝗯𝘀𝗶𝘁𝗲 𝗺𝗮𝗸𝗲𝘀 𝗳𝗼𝗿 𝘁𝗵𝗲𝗺.
 
They assume the same level of polish and thought put into your website go into your product, too.
😒 If the design feels dated, they assume the product UI is clunky.
😒 If product screen shots feel too mocked up, they assume the product isn't robust enough.
😒 If it's hard to figure out what you do, they assume the product is just as convoluted.

A lot of teams either go full nuclear on a redesign and lose everything distinctive about their brand, or they're so precious about what they have that the "redesign" is just a fresh coat of paint on the same old house.
 
So when Josh and I sat down to figure out what to actually change, we built three buckets.
 
𝗕𝘂𝗰𝗸𝗲𝘁 𝟭: 𝗞𝗲𝗲𝗽. These are the things that make you you. The stuff your audience would immediately recognize and miss if it disappeared. You don't want to lose them—you want to evolve them. Same personality, better haircut. For us: Ghostie, bright colors, bold statements with a wink.
 
𝗕𝘂𝗰𝗸𝗲𝘁 𝟮: 𝗚𝗹𝗼𝘄 𝘂𝗽. These are the things that aren't bad, exactly—they're just limiting. They paint you into a corner or kill your flexibility, even if people associate them with your brand. For us: super saturated color usage that made text basically impossible to read.
 
𝗕𝘂𝗰𝗸𝗲𝘁 𝟯: 𝗥𝗲𝗽𝗹𝗮𝗰𝗲. These are the things actively working against you. They're building a perception you don't want—making you look smaller or less sophisticated than you actually are. No sentimentality. They gotta go. For us: all-caps headlines and ghost visuals in spots that should have had actual product screenshots.

The reason I love this framework is it gives you permission to make bold changes while protecting the things that actually matter. Before we kicked off the project with our design agency, Josh and I literally listed out which parts of our brand fell into which bucket. It made every every design decision after that so much cleaner. 🤌

The FULL second season of is out now! Just search This Meeting Could've Been a Podcast.

Nick Zeckets

Nick is a product-driven growth leader with experience at the executive leadership level for large publicly traded companies as well as being a serial founder and CEO (two MarTech exits) and currently running Smoke Signals AI - the first AI-first HubSpot agency that wraps content, signals, AI and workflows into programs that generate real pipeline.

CEO, co-founder

This is the most exciting work I've ever had the pleasure of being a part of.

At Air Traffic Control, our team has enabled any marketing software from email to web with personalization features. Not segments. Not logic building. True machine learning that dynamically serves up content, products, and anything else a customer can dream up to *each* person.

We're growing rapidly and I welcome the opportunity to share our vision for mass-personalization with you.

I showed a few friends a HubSpot app I'm building and response has been universally positive (probably because everyone's blowing smoke?).

Here's what it does.

You connect it to your HubSpot account. It pulls every deal you've ever closed, won or lost. Every activity. Every attribute. Then it goes out and researches each account and comes back with a scoring model across dimensions like velocity, expansion potential, and fit.

But the real value is the prescriptive layer. Because if we know where an account has gaps, we can trigger HubSpot workflows to fill them automatically. 

No one has to remember. No one has to check a spreadsheet. It just runs.

I built the full interactive UI mockup in twenty minutes using Claude. React components, HubSpot sidebar previews, onboarding flows, the whole thing. The PRD came out of a conversation where I gave it my reference docs and tribal knowledge about what makes a great ICP analysis.

When you show someone their own closed-won data organized in a way they've never seen before, with next steps already queued up, the reaction is always the same.

Not better dashboards. Better systems that act on the data without waiting for a human to notice.

If you want more details on our plans for this, comment "ICP" below and I'll share a walkthrough.

Most GTM AI is nonsense. Let's clear things up.

We're hiring a fractional HubSpot/RevOps Operator at Smoke Signals AI.

~20 hours/week. Remote. $50-75/hr.

Here's the role:

We build signal-based go-to-market systems for B2B companies. HubSpot is the system of record for every client we work with. The RevOps Operator is the person who keeps those portals running cleanly and powerfully across multiple accounts.

This is hands-on, in-the-portal work. Every week. Not strategy decks. Not audits that sit in a Google Doc. You build workflows, sequences, reports, dashboards, and integrations. You manage data hygiene, lifecycle logic, and lead scoring. When native features aren't enough, you build private apps and UI extensions to fill the gap.

What I care about:

- You have 3+ years of real HubSpot experience. Not certifications. Not "I've used it." You've built complex workflows yourself and can walk me through the business problem, what you built, and what happened.
- You've gone beyond native features. You've built private HubSpot apps and UI extensions. You understand the developer platform, not just the drag-and-drop builder.
- You've worked across multiple client accounts at the same time. Agency or freelance background preferred. You know how to pick up context fast and switch between portals without losing the thread.
- You can work across Sales Hub, Marketing Hub, and Content Hub. Not just one.

This is a weekly-delivery environment. Every Friday you share what you shipped across your client accounts. Not what you worked on. What you shipped. If you thrive with that kind of accountability, you'll love it here. If you need long runways and open timelines, this isn't the right fit.

Small team. No layers. You work directly with me from day one.

Apply here: https://lnkd.in/eu5PvX5M

If you know a HubSpot operator who actually builds, I'd appreciate the tag.

Open article: RevOps Fractional Role Application by smokesignals.ai

I accidentally discovered a sales motion that converts better than any cold outreach I've ever run.

I ask someone who fits my ideal customer profile (but isn't a customer/live prospect) to introduce me to another person who fits my ideal customer profile. I explain who I'm trying to reach and why.

And then something interesting happens.

About half the time, they stop and say "wait, can you tell me again what you're doing now?"

They hear the use case. They realize they have the exact problem I'm describing. And they book a call themselves.

It's a psychological backdoor. You're not pitching them. You're asking for help. But in explaining why someone else needs what you do, you're giving them the clearest possible description of your value, without any of the pressure that comes with a direct pitch.

The introduction request is the pitch. You just never frame it that way.
If your ICP knows other ICPs (and they always do), this is the warmest cold outreach you'll ever run.

I want a LinkedIn tool that evaluates comments on my posts to tell me if they’re LLM nonsense.

I spend a lot of time in my comments section. I want to add value there. Connect. Get to know new people and old connections better.

The AI comments are sometimes obvious. But sometimes not. Spending time trying to figure out if I should reply to something is a terrible use of my time.

But I’ll say this: if I have a hard time building on someone’s comment, that’s usually a very good sign it’s AI or, at least, lazy.

15 sales calls for this week. A lunch with 70 revenue leaders on Thursday. Two apps to push (one deployed, one baking).

Things are seriously heating up at Smoke Signals AI. 😳

There's a serious problem with the GTM Engineering role.

I recently posted that we're looking for a halftime GTM E to support our rapidly expanding base of incredible customers.

The application page asks applicants for one of their more powerful workflows.

We have about 50 applications so far and here's how it breaks down:

Tier 1 (2 of these): workflows that not only involved cleverly designed signals at the core of the workflow, but produced *real* results.

Tier 2 (30 of these): basic workflows, all done in Clay and some mass email tool like Smartlead or Instantly, celebrating open rates.

Tier 3 (20 of these): simple enrichment tables in Clay.

Folks, you can use Clay's Sculptor feature to do the Tier 3 stuff in 5 minutes. Seriously. This isn't a person. It's a 5 minute bot chat.

Tier 2 work doesn't change anything. It isn't unique. It's just a more efficient approach to doing what good GTM teams have done for YEARS.

Tier 1 is the only thing that matters. Stop hiring for or building anything else.

Now, that doesn't mean you can't train a tier 2 or 3 GTM E into doing Tier 1 work. Everyone has to start somewhere.

But if you're going to "hire a GTM Engineer" and think things are going to change for you, the data dictates you're *most likely* wrong.

The critical missing piece is actually having a complete framework for how GTME work fits into a robust GTM operating system. It is not one unto itself. It's part of a broader matrix of market understanding, content and trust, sales enablement, and signals. (which is exactly what we design at Smoke Signals AI)

We're hiring a fractional GTM Engineer at Smoke Signals AI.

~20 hours/week. Remote. $75-125/hr.

Here's what the role actually is:

We build signal-based go-to-market systems for B2B companies. Not intent data. Not buying committees from a database. Proprietary signals that identify when a company is experiencing a specific pain, before they start Googling for solutions.

The GTM Engineer is the person who builds that intelligence layer. You design the enrichment pipelines, create AI agents in Claude for research and personalization, connect external APIs to HubSpot, and architect the data flow that makes the whole thing work.

Our stack is Clay, Claude, HubSpot, and custom integrations. No middleware. No Zapier spaghetti.

What I care about:

- You use Claude every day. Not as a chatbot. As a building tool for agent workflows, prospect research, and content generation.
- You can read API docs and build integrations without someone holding your hand.
- You know Clay well, but you also know when Clay isn't the right tool and something custom is needed.
- You've built at least one real system that combined enrichment, AI, and CRM automation to produce pipeline. Not a demo. Not a proof of concept. Something that generated meetings.

This is a weekly-delivery environment. Every Friday you share what you shipped. If that sounds stressful, this isn't the right fit. If that sounds like how you already work, we should talk.

You'll work directly with me across multiple B2B client accounts doing some of the most interesting signal work in the market right now.

Apply here: https://lnkd.in/eNiesmCw

If you know someone who fits, I'd appreciate the tag.

Open article: Fractional GTM Engineer Job Posting by smokesignals.ai

When I first pitched the idea of an executive lunch where every speaker has to show real AI metrics, I wasn't sure anyone would come.

We confirmed 50 of 70 seats in the first two weeks.

Turns out revenue leaders are starving for honest conversation about what's working. Not another webinar. Not another vendor demo disguised as a panel. A real meal with real peers talking about real results.

February 26. Davio's Back Bay. Boston.

Still looking for two more speakers who have deployed AI in their GTM motion and are willing to share the numbers. Comment "speaker" if that's you.

Seats are going fast. Comment "Boston" for the registration link.

So, we have our Receipts: AI in GTM lunch and we've hacked a way to identify ideal event attendees from registrants' LinkedIn networks using Clustr.

First, Clust allows you upload, webhook in, or just paste a LinkedIn profile. Then it looks to see what people are engaging with those profiles and have overlaps in work experience and fit your ICP.

From there, we pass it to Clay to further filter on things like the person's location (it's a lunch event and we're paying, but no one's likely to fly in for a 2 hour event so local folks are key), tech use, etc.

Then ping the registrant with the 2-5 great event attendee fits and say they can extend invites to those people to be their guests. They get to do their network a solid. We keep the ask very focused. And the room becomes even more curated with world-class revenue leaders.

Event reg link is here, by the way:

https://lnkd.in/eaQF4e5C

Most B2B companies skip the step that makes everything else work.

They jump straight to outbound. Cold emails, LinkedIn sequences, ad campaigns. And then they wonder why response rates are terrible and pipeline feels random.

Here's what we build first at Smoke Signals before a single message goes out.
A product marketing foundation. Use case libraries, messaging hierarchies, positioning docs, jobs-to-be-done narratives. The stuff that gives AI and automation the context they need to actually be useful. Without it, you're just blasting generic copy faster.

Once that foundation exists, we start listening for signal. Not intent data you buy from a vendor that your competitors also bought. Alpha signals. Proprietary data we pull through Clay, APIs, data scrapes, fire crawls. Things that tell us a company is in a buying window right now, not that someone at the company googled a keyword six weeks ago.

From there, we score ICP fit and check for warm paths in first. Existing connections. Partner intros through SoundGTM. Only when there's no warm path do we go cold. And when we do, the outreach is built on the PMM context and tied directly to the pain signal we detected.

That's why our response rates are remarkably high compared to what most teams see. Every message is connected to a real signal, written against real positioning, and sent at the right moment.

This is the GTM operating system we install for every client. Not a campaign. Not a playbook. A system that compounds.

If you want to see the full breakdown of how this works, comment "GTM" below.

Had a conversation with 🤘 Matthew Sciannella from Refine Labs this week that got me thinking about a structural problem in enterprise marketing.

Most enterprise marketing teams are trapped in an incentive loop. The way budgets work at large companies, the surest way to lose your budget next year is to leave money on the table this year. So the rational move is to spend it all and report on activity. Impressions served. Campaigns launched. Budget utilized.

It's not a competence problem. It's an incentive design problem. And it punishes the exact behavior that would make marketing more effective.

Matthew's team actually pushes clients toward geo-based lift tests. Pick two similar markets. Run the campaign in one. Leave the other alone. Measure the difference in meetings booked over six weeks. Simple, rigorous, and it gives you a real answer about what the spend did.

But running that test takes courage. Because the result might say the campaign didn't move the needle. And in a system that rewards spend over proof, that's a dangerous finding to surface.

This is why smaller companies with tighter budgets often outperform enterprises on pipeline efficiency. They can't afford to not measure. Every dollar has to prove itself.

The teams that break out of this loop are the ones who shift from "did we spend it" to "did it work." That's a leadership decision, not a marketing ops fix.

If you're trying to build a go-to-market program where every signal and every touch is tied to a measurable outcome, comment "signals" and I'll share how we structure it for clients.

We're hiring at Smoke Signals, and I wanted to share how we're actually going about it because I think there are some lessons here for early-stage founders.

When we opened up roles for HubSpot RevOps and GTM engineers, we got dozens of applications. Way too much information to process manually. And we're too small for an ATS. We're not hiring all the time, so that investment doesn't make sense.

What to do?

Dump all the application data from our HubSpot applicant form into Claude, then I gave it the job description, and asked it to rank order everyone.

It scored candidates zero to 10 across HubSpot depth, private app development experience, business problem understanding, specificity and credibility, and overall role fit. Then it broke them into tiers: must interview, strong, maybe, and pass.

That gave us three top candidates. Straight to the call, right? NOPE.

Our next step isn't a traditional interview. It's a paid project. Two-day window, not two days of work, something reasonable that tests real skills. We pay on delivery regardless of whether they get the role. We're not asking people to do free work and then ghosting them.

How are we grading it? Did they get it done? Does it work? Did they go above and beyond, iterate, come up with something clever, push the project further than we asked?

That tells us more about speed and acumen than any certification ever could. I could not care less about HubSpot certifications. You could have Claude Cowork take every single one for you and get a perfect score. Means nothing.

I want to see you build something. And I don't care if you use AI to do it. If you can build something great that delivers real value in under two days, you've got chops.

Then we get to know you as a person and see if there's a fit.

Hiring is hard when you're early stage with no HR partner and no budget for enterprise recruiting tools. But between Claude for prioritization, HubSpot forms for intake, and paid projects for evaluation, you can build a process that actually works.

I cannot stress this enough...

If you think there's something wrong, there is.

I have a track record of either (a) working 10x to blast through a rough patch or (b) giving people waaaaaaay too much rope.

The first rarely works out. Once you're in fight or flight mode, work volume might increase, but quality does not.

The second... it's rarely the other person who gets hung with that rope.

I'm no CEO whisperer. By any means. (in fact, for the first time in my life I said out loud, "I think I'm ready for a CEO coach" just yesterday).

But I am scarred and willing to talk about how I got them.

Peep Laja had a really compelling post on what B2B SaaS CMOs are focused on right now. But I think the bigger story kinda got lost in the narrative.

AI doesn't mean anything.

Automation doesn't mean anything.

Neither does ABM. Or intent data.

But if you look across all of these data points, what you'll see is an emerging sense amongst revenue leaders that something very important is happening and I'd split it into two macro themes:

1) Signal, combined with AI and orchestration tools, is the unifying force GTM has bee looking for. Finally, marketing, sales and CS are able to grow *together* in ways that has *never* been possible.

2) And by doing that, we're able to get out in front of our customers IRL. Events. Yeah. But I'm going to say right now that sales rep T&E budgets are getting ready to explode (in the best run sales orgs) because we're able to qualify the value of that plane ticket. Of that long lunch or small group dinner. We *know* who trusts us and is deeply interested in the problems we solve like we have NEVER known before.

Come talk to me and my team at Smoke Signals AI about the first one so you and your team can do the second one.

h/t Evan Dunn for pointing me at this post of Peep's.

I'm building an event series called Receipts and I want to share why.

The B2B events space has a trust problem. Sponsors pay for stage time. Speakers deliver thinly veiled product demos. Attendees leave with a bag of swag and zero actionable insight.

Receipts flips the model. We curate the audience (CROs, CMOs, VPs only). We pick speakers based on what they've actually done, not who paid. And we ask every speaker to show real numbers, real timelines, real outcomes.

The first Boston edition is February 26 at Davio's Back Bay. 70 seats, about 20 remaining.

If this is the kind of event you wish existed, comment "Boston" and I'll send the link.

I've had a Clustr tab open in my browser for two weeks straight. And it's the reason our executive lunch next Thursday is almost full.

Every time someone registers for Receipts, our invite-only lunch for VPs of marketing, CMOs, and CROs, I drop their LinkedIn into Clustr. It maps their professional network and scores each connection by relationship strength.

Anyone above 75% confidence who's in Boston and matches VP-plus seniority gets flagged. I send the registrant a note: "These 3 people look like they'd love to join you. Invite them as your guest."

Those guests register. I drop them into Clustr. Find their connections. Repeat.
Almost all of our top-tier attendees came through this chain of warm referrals, not through event marketing. The quality of the room went up with every wave.

We're at 54 confirmed for 70 seats. Next Thursday, February 26, in Boston. No vendor pitches. No panels. Just senior revenue leaders having real conversations over a nice meal.

If you're a VP-plus in marketing, sales leadership, or revenue operations and you're in the Boston area, we have a few seats left. Comment "Boston" or DM me and I'll send the details.

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