Rob Charlebois

Sectigo

VP of Growth

LastPass

LastPass provides password and identity management solutions that are convenient, easy to manage, and effortless to use, helping millions of users organize and protect their online lives. From enterprise password management and single sign-on to adaptive multi-factor authentication, LastPass Business gives superior control to IT and frictionless access to tens of thousands of businesses.

Led corporate marketing (public relations, brand, creative, events, organic social), demand gen and field marketing, product marketing, growth marketing, lifecycle marketing, content marketing, product-led growth, marketing analytics, marketing tech, marketing operations, creative, and website strategy (production, tech SEO, a/b testing, user experience).  Accountable for marketing pipeline, eCommerce self-serve revenue, marketing budget, and all key marketing KPIs. Team of +70.

Chief Marketing Officer

WP Engine

As a member of the T1 executive leadership, I was accountable for self-serve revenue and growing leads, generating qualified opportunities, and increasing the pipeline for WP Engine's SMB, Agency, and Enterprise segments. I left due to personal reasons but my teams launched several high-impact initiatives, which included:

▪️ Partnered with a world-class media agency to grow paid media and organic search
▪️ Overhauled the creative process to improve efficiency, prioritization, and alignment 
▪️ Accelerated A/B testing velocity and implemented a test and learn methodology to increase the impact
▪️ Launched a website rebrand/redesign to support an upmarket shift 
▪️ Optimized website chat programs with improved dashboards, trigger rules, qualification criteria
▪️ Refined approach for the weekly self-serve revenue and opportunities forecast 
▪️ Created a tiger team to improve Google desktop and mobile lighthouse page speed to over 90
▪️ Led the internal creative agency; responsible for company-wide creative, web, video, and content production
▪️ Led paid media programs; including PPC, display, paid social, affiliate, and ABM programs
▪️ Led marketing operations; including email campaigns, lead harvesting, routing, and virtual events
▪️ Team size ~50 passionate and dedicated marketers

Senior Vice President of Digital

Corel Corporation

As a key go-to-market leader on the executive team, I drove bookings and recurring revenue growth across the organization. I grew enterprise value and played a key role in selling Corel to KKR for $1.1B in 2019. 

My P&L responsibility included $175M in top-line bookings, a $45M paid media budget, and 90 marketing, creative professionals, developers, and data analysts. Central to my role was owning the ROI of marketing investments, building end-user awareness, and revenue growth across all channels, including self-serve eCommerce, retail, VAR, and enterprise licensing.

Leveraging my deep expertise in digital marketing, data analytics, and strong technical knowledge, I implemented hypothesis-driven growth initiatives that extended product capabilities, improved product messaging, and built frameworks for measured execution. 

Corel is a high-velocity business that produces over 2M orders per year, across 100+ products, on 35 websites and at a blended AOV of $93. Our localized approach included 12-20 languages, and we processed subscriptions in 23 localized payment methods in almost every country.

As a player coach, I worked closely with my leadership team to equip our teams with precise goals, knowledge, and the tools they needed to succeed, develop mastery, and ultimately reach their full potential.

EVP of Global Digital Marketing & eCommerce (Acquired for $1.1B by KKR)

During this period in Corel's evolution, rapid and profitable revenue growth was our goal to meet our private equity owners' EBITDA targets,  fund our acquisition strategy, and accelerate the turnaround.

Our team ran growth and optimization playbooks to reinvigorate sales for Corel brands that had plateaued. Our track record of successful revenue growth in desktop utilities created an opportunity to acquire one of our competitors, improve gross margins, and own our code to improve user engagement, conversion, and signal significantly.

I was ultimately accountable for exceeding revenue targets, meeting expense goals, and building end-user awareness to support broader cross-channel revenue growth. In addition to revenue, my creative, web production, development, and IT teams focused on building enabling technology to support engagement, retention, and conversion programs.

Growing a portfolio of product-led freemium and free trial products took deep expertise in analytics to measure cohort-based performance, triggered in-app notifications, and structured hypothesis-driven execution. 

Highlights:
▪️ Built a $25M ARR desktop utilities business with ~25 software titles across three separate brands
▪️ Architected a "no user left behind" strategy that expanded user reach and revenue significantly by extending in-product messaging to inactive users
▪️ Led the shift to subscription for WinZip and tripled LTV
▪️ Optimized product discovery and user retention to reduce CAC
▪️  Exceeded YoY targets and grew revenue by a CAGR of 4.5%
▪️ 22% YoY growth in organic SEO by breaking Corel.com into ten micro-brand websites
▪️ Drove incremental revenue by expanding brands into new countries and languages
▪️ Engaged with industry leaders to influence Google Safe Browsing, Clean Software Alliance, and CleanApps policies

VP of Online Sales & Marketing (Acquisition, Monetization, Retention, Analytics, Martech)

Chosen by General Manager to apply the data-driven growth playbook developed in previous roles. Tasked with breaking down legacy mentality and transforming e-commerce and digital marketing functions. Quickly promoted with full accountability for achieving sales targets and growing net new revenue streams. Led annual planning and execution, developing and upskilling ~15 marketing professionals, web producers, and web developers while building influence, customer service, and product teams.

IMPACT: Increased direct sales by 6% YOY and partner program revenue by 48% by building out and transforming technical infrastructure for sales and marketing, instituting digital marketing and e-commerce best practices, and creating a nimble, responsive, and growth-centric organization. Grew third-party revenue 102% by negotiating $3M in advertising revenue. Identified and led full cycle acquisition of a utilities business that launched three distinct brands, WinZip Utilities, Reviversoft, and SimpleStar which now consist of over 25 software titles.

Expertise:
▪️ Co-marketing, distribution strategy, channel optimization
▪️ Global M&A, acquisition integration, & acquisition optimization
▪️ Global product launches, program management & strategy
▪️ Contract negotiator, technology buyer, and systems integrator
▪️ Technology & marketing platform development strategy
▪️ In-app messaging, software installation optimization, and software analytics

Sr Director Of Global eCommerce - WinZip

Recently acquired by Vector Capital, Corel was in acquisition mode, which led to growth through the acquisition and integration of two Taiwanese companies  (Ulead, Roxio), products, websites, and respective technologies and teams. Built team from 3 to 25, with accountability for multi-million-dollar annual revenue target. Tasked with building growing paid acquisition programs, organic acquisition, integrated marketing campaigns, and building accretive value through cross-selling, upsell, and expansion programs.

IMPACT: Grew revenue by 14% YOY, affiliate program sales 127%, and email marketing sales 80%. Expanded shopping carts to 224 countries, which entailed coordinating with individual local workflows. Led digital integration of Jasc and Ulead.

Director of eCommerce, Americas - Corel (Go-Private)

Senior eCommerce Manager - Americas - Corel (IPO - 2006)

Softchoice (Formerly ComputerLand.ca a division of NexInnovations)

Worked side-by-side with Bruce Linton (Canopy Growth) to re-launch the ComputerLand brand in Canada and deliver high-quality IT software, support, and services to SMBs. My key responsibilities included driving awareness and monetization campaigns through performance marketing channels and traditional media; working closely with development teams to build a strong platform and compelling user experience. We built one of the largest eCommerce catalogs in the country drawing inventory from 3 major distributors and integrating services from Nexinnovations.

Sr. eCommerce Product Manager

N-able

N-able Technologies (now SolarWinds N-Central) created solutions specifically designed for IT service organizations, MSPs, and value-added resellers (VARs) to offer customers centralized network management and remote network monitoring solution. In my role as a product line manager, I created market-driven requirements documents, delivered sales presentations to MSP partners, and worked closely with development teams to build customer-driven products and programs.

Product Line Manager - N-Central IT

Buystream

Buystream.com was a venture-backed, tag-based, digital analytics start-up that helped marketers measure key digital marketing metrics for marketing, web, and E-Commerce programs including web traffic trends, conversion rates, and user profiles. During my time at Buystream, I defined created product marketing requirements, worked with product teams to release customer-driven features, and built an agency channel sales program.

Product Manager - Buystream - Web Analytics Software

Rob Charlebois is a marketing executive with over 20 years of experience in leading global marketing teams and driving revenue and user growth for private equity owned technology businesses. He is currently the VP of Growth at Sectigo, a leading provider of digital identity solutions and web security products.

As the VP of Growth, Rob is responsible for overseeing the digital marketing funnel, from awareness and acquisition to retention for the retail segment. He leverages data, analytics, and experimentation to optimize the customer journey, enhance the brand identity, and increase the market share of Sectigo. Prior to joining Sectigo, Rob was the Chief Marketing Officer at LastPass, where he transformed the customer experience and aligned the marketing organization with the business goals. He also held executive leadership roles at WP Engine and Corel, where he led demand generation, growth marketing, platform development, and more. Rob has a proven track record of increasing enterprise value for private equity owned businesses.

LastPass provides password and identity management solutions that are convenient, easy to manage and effortless to use, helping more millions of users organize and protect their online lives. From enterprise password management and single sign-on to adaptive multi-factor authentication, LastPass Business gives superior control to IT and frictionless access to tens of thousands of businesses.

Aligned

Head of Marketing

Clay

Content Creator

Lewin Investments, LLC

Managing Partner: Derick Lewin
Partner: Ashley Lewin

- Managing and growing an investment portfolio of properties in the Omaha, NE area
- 6 single-family residential units 100% owned
- 10 additional residential units owned jointly in partnerships 
- 8 commercial buildings totaling over 130,000 SF of office & retail space

Partner

Wix Studio

Advisory Board Member

Refine Labs

‣ Revenue Performance Strategy: Designed and led Revenue Performance Assessments for enterprise clients, auditing $1 billion+ in pipeline across eight companies and creating actionable plans to optimize revenue sources for efficient growth. Delivered tailored GTM execution roadmaps that drove profitable funnel improvements for clients, including Recorded Future, Criteo, Workiva, Checkr, Amperity, Cylindo, Beamery, New Store, and Axonius.

‣ Demand Generation Consulting: Partnered as a strategic advisor to VP+ executives at 20+ organizations, transforming demand generation strategies through in-depth GTM analysis, marketing operations optimization, ABM frameworks, digital advertising, and lead handoff audits. Key outcomes include a 46% increase in hand-raisers and 59% growth in qualified pipeline for one of the clients within one year. Additional clients include Blackline, Syndio, Algolia, Cognism, Canva, Hopin, IBM Instana, Typeform, and Braze.

‣ Helped develop and launch a new offering: The Vault. Contributed to ICP refinement, messaging, and go-to-market strategies. Played a key role in product development, marketing, and customer advisory for the product. Today, The Vault supports 5,000+ B2B marketers by delivering essential resources, playbooks, and templates to streamline growth and reduce customer acquisition costs.

‣ People Management & Team Mentoring: Led, coached, and fostered growth within a team of high-performing performance marketing managers. Focused on developing strategic thinking and executional skills through hands-on coaching in demand gen best practices, data-driven decision-making, and campaign optimization. Built a collaborative and growth-oriented environment, enabling team members to exceed performance targets while aligning with organizational goals.

Sr. Director of Demand Generation

Director of Demand Generation

Consult with small businesses on how their marketing strategies, specifically technical paid media management, are being managed to increase leads/conversions, reduce CAC, and gain more revenue

Marketing Advisor

Demand Generation Manager

Flywheel

Growth Lead

- Built and implemented a digital advertising program that heavily impacted all revenue streams
- Owned Flywheel’s website optimization, marketing automation, lead generation program, and digital advertising efforts
- Continuously brainstormed, tested, and executed optimization experiments to improve channel performance and drive profitable growth 
- Worked with the sales team to create lead generation strategies and support the sales pipeline with marketing resources
- Analyzed marketing campaign data and ran A/B tests to regularly assess ongoing value of acquisition efforts
- Helped the content and design teams create targeted campaigns.

Marketing Strategist

Social Media Specialist

SKAR Advertising

•	Strategized retail, government and healthcare clients' social media accounts
•	Project managed all digital projects, such as website and mobile applications, from start to completion

Digital Content Manager

Scooter's Coffee

Held a variety of roles including public relations, social media, advertising, copywriting, project management, web strategy, and print design to help grow a national franchise and distribution company go from seven states and under 100 stores to 40 states with 150+ stores

Social Media Specialist & Graphic Design Coordinator

Marketing Intern

Demand Generation Leader | Marketing | Growth | SaaS | B2B

Modern growth marketer with a proven track record of growing inbound revenue through proper demand generation for SaaS and B2B models. Constantly challenging traditional marketing tactics, and is data-inspired, not data-driven. Experienced with helping to build revenue, go-to-market, marketing, and digital advertising plans that drive real results.

Ashley Lewin

I’ve seen a lot of really talented B2B SaaS/tech marketers unable to move up in their career because they haven’t mastered this yet:

👉 Understanding (and being comfortable inside) a CRM.
Primarily HubSpot or SFDC.

Here’s why it matters so much:

1. Reporting lives there.
→ You don’t have to be the resident expert, but you do need to be self-sufficient. The higher you go in your career, the more you’re expected to pull your own data.

2. Insights live there too.
→ Reporting is one thing — but understanding the fields you track (or should be tracking) is how you uncover ideas, diagnose issues, and build stronger campaigns. Every company’s setup is unique.

3. Leads, opportunities, and revenue all sit in the CRM.
→ If you want to speak confidently about pipeline and performance, you have to understand the system behind it.

I stumbled into becoming the marketing HubSpot admin in my first tech role.
No formal training. No courses. Just a lot of trial, error, and curiosity.
And once you learn one CRM, picking up others becomes easier.
(Except Pardot — I still don’t fully understand you 😆. And Marketo… why are you like this?)

With AI now, there’s truly no excuse not to teach yourself.

If I didn’t feel confident navigating a CRM, here’s exactly what I’d do:

→ Dedicate 1–2 hours a week to clicking around in contacts, deals, accounts, fields, workflows — all of it. Get familiar with what exists.

→ Schedule learning time with the CRM-savvy person on your team.
Come prepared. Use the time wisely. Bring very specific questions.

→Read up on objects and how they relate.
This alone clears up 50% of confusion.

→ Use AI as your tutor.
Ask it to explain fields, objects, logic, and reporting. 
(Pre-AI, I lived on Google and community forums.)

→ Start building simple reports.
You learn fastest by doing. 

Learning these systems isn’t glamorous. It requires time, curiosity, and a lot of questions. But like it or not, it’s a core skill for climbing the marketing leadership ladder in B2B SaaS.

Pipeline crisis chatter is taking over my marketing LinkedIn feed. Here’s my observations and the tactical actions worth considering right now. 

1. Buyer behavior has shifted. Opp volume might be lower, but quality is higher.

Buyers are self-educating more than ever.
They are using AI tools, searching for ungated resources, watching interactive demos, talking to peers, and gathering context long before they show up in your CRM.

By the time they raise their hand, they already know what they want to learn.
If you make the shortlist, they are warm. They are in an active decision cycle. The question becomes how fast you can support them with clarity and zero friction.

About a month ago, Matt Green (CRO at Sales Assembly) shared something that confirmed this. He got off a call with HubSpot where they reviewed data across their customer base. Deal volume was down year over year, close rates were up, and net pipeline was holding steady. The intent is still there. Buyers are simply showing up later and more qualified.

I will drop his post in the comments because it is a great one for sales on how to act on this moment too.

ACTIONS TO TAKE:
→ Audit your content for real buyer self-service
→ Add an interactive product demo
→ Create zero click content that prioritizes distribution
→ Lean into creators, influencers, and referral programs
→ Review BDR outreach for quality, research, and context
→ Keep lessening the team’s dependency on attribution so you can run marketing that catches their attention and helps them. It should be 0 click, and won’t show in attribution, but that’s how you get in their head while they’re self educating
→ Tighten your hand raiser flow with instant booking and faster follow up
→ Bonus idea: send a deal room like Aligned so buyers have everything they need while they wait with a surprise + delight white glove service to project manage the process as a differentiator (special offer in comments)
→ Measure qualified pipeline with a 25% win rate instead of chasing raw opp creation

2. Most teams fixate on net new even though the fastest conversions are already in the system.

The moment pipeline dips, teams sprint toward new leads. But the highest quality and fastest moving revenue often comes from contacts and accounts you already touched. Most teams miss strong signals because they are only tracking new activity.

ACTIONS TO TAKE
→ Sit down with your favorite drink and manually review your CRM
→ Identify what automation is missing
→ Make notes on patterns and signals for outreach
→ Build follow-ups for these leads
→ Review closed lost and launch ongoing campaigns

& yes, it feels harder.

What worked 6 months ago has already aged.
Buyers are faster. Markets are noisier. AI has flooded every channel with more content than anyone can process.

When it feels chaotic, zoom out and use common sense. What would you want as a buyer.
Where is the friction.

Serve your audience, not your process.

In June I outlined an experiment I used to roll my eyes at: webinars. 🫣
6 months later, they’ve proven their impact. Not the fluffy, talk-at-you kind of webinars, but the deeply tactical, helpful, well-prepared ones.

Whenever I run a new experiment, I want strong signals before investing time or resources.
So we approached webinars with an MVP mindset: prove it out first, then scale.

Full transparency: I used to be semi-allergic to the word “webinar.”
(Okay, dramatic. But still true.)

What changed was how we approached them — in a way that fit our 3 core marketing principles:

1. Teach, don’t fluff
Practical, tactical education buyers can use right away.

2. Help GTM teams win
We want GTM and sales teams to crush quotas and get paid more.
We’re just one piece of that puzzle.

3. Be human (with a 😉)
Relatable, engaging, encouraging — we talk with GTM teams, not at them.

So instead of broad, theoretical webinars, we narrowed every session to a specific problem.
We partnered with an expert.
We built a meaty, tactical deck you could basically turn into a guide.
And we spent the session walking through it, leaving plenty of time for questions.
Our chat is lively every single time.

The results?
We’re still building out the right reporting, but the qualitative signals are strong:
→ 700–800+ registrants with minimal promotion
→ ~30% attendance rate
→ Consistent market feedback about how tactical and “actually helpful” they are
→ Showing great patterns of great attendees/companies, showing up in sign ups, pipeline, open opps, current customers, and even a correlation with self-serve purchases

This is great for the live experience.
But I'll let you in on where we're not doing so great:

Our post-event workflow has been… meh.
(Small team. Lots of priorities. The usual.)

Here’s what we currently do:
→ Create a post-event Aligned deal room with the recording, deck, resources, and a promo
→ Send a simple follow-up email from me
→ BDRs action the right accounts (somewhat generically)

It works, but it’s nowhere near what this content could be doing.
We haven’t been fully repurposing the content gold we’re creating — and I want to change that as this becomes an always-on program.

This is where tools like Tofu help teams like mine turn a one-time moment into a content machine, without adding a ton of more hours to your already packed schedule.

With Tofu you can:
→ Upload your recording and generate deep account + contact intelligence with Tofu’s research agent
→ Identify pain points from the session
→ Craft unique, 1:1 nurture that actually speaks to the contact 
→ Extract highlights, quotes, stats, timestamps
→ Turn one webinar into: blog posts, social content, attendee follow-up, nurture for no-shows, ads for on-demand content, and more

Talk about a time saver (!).

We’re still early in maturing this program, but I’m excited — because tools like Tofu help small teams do what they actually want to do, not just what they have time for.

#TofuPartner

Brand partnership • Head of Marketing at Aligned

Is Demand Gen just paid and new business? A CMO asked me this when I was in the interview circuit. After our conversation, I left the team with a little “leave-behind” doc to unpack it.

Because honestly… the role is so fuzzy.

And I’ll admit: I got burnt out on it for a while.
Not from the work, but from all the debates.
What counts, what doesn’t count, who owns what, and being cornered into only paid, only capture demand, only new acquisition. 
(Nobody puts baby in the corner, let me have more fun! (I hope others catch that movie quote))

But here’s what I’ve landed on:

The role is defined by you and the company, not the internet.
Once I embraced that, I got a much needed reset.

So after that interview, I put together a doc for the marketing team, the leader, and the CEO to make the role a little less fuzzy, and define it my way. 

It included:
→ how I define demand gen
→ the metrics I’d own
→ how it fits across Sales, CS, PMM, and RevOps → what roles would report into it
→ the balance of always-on work + special campaigns
→ and one special campaign example based on a real expansion gap they had

(Attached that section of the doc here if it’s helpful. It isn’t polished as if I were executing it. I find those imperfect examples are the most useful to flip through to spark inspo.)

I talked about my idea of Focus Cycles last week, and this is a perfect example of putting them into motion.

Because this is the kind of DG work that gets me excited.
Not just channels.
Not just “fill the funnel.”

But spotting strategic opportunities → framing them → and turning them into cross-functional special projects that move the business forward.

And sure, you could argue this work lives in campaigns, growth, or general marketing leadership.
Maybe in your company it does.

That’s the whole point.

Demand Gen can be more than paid, more than new business, and more than capture demand. it’s shaped by your team size, structure, and the revenue gaps that actually matter.

Attached the example if you want to skim it.

Where do you think DG’s scope tends to get limited the most? Are you running special campaigns like this, and who owns them? 

(PS - If you’re interviewing, this type of additional effort will make you stand out!)

Special Campaigns Brief Example

Saw a post from a dad listing the majors he does not want his daughter to pursue.

→ Marketing
→ Communications
→ Design
→ Philosophy
→ Accounting
(& a few others)

His belief is that AI will take those jobs. (And can't fault him for wanting what's best for his kid!)

I was stunned, not because I'm a marketer and took it personally, but because that logic feels so upside down.

A few hours later, I saw a Brené Brown clip with a completely different perspective.

She said she has been fortunate to be in rooms with wildly successful people like founders and executives. She asked them what they study and what interests them.

Their answers:
→ Philosophy
→ Arts
→ History

Deep thinking, pattern recognition, human behavior
The exact fields that dad wants his daughter to avoid.

She mentioned tech legends like Steve Jobs whose kids did not have iPads, and how their dinner conversations were about art and ideas, not technology.

Lesson from this:
→ Your tools will change.
→ Your thinking will not.

And that is where this gets interesting.

Whether it's communications, marketing, design, philosophy… these are not “AI vulnerable” fields.

They are how people learn to:
→ think clearly
→ interpret nuance
→ understand humans
→ communicate ideas that land
→ navigate change
→ build meaning, not just output

These are the skills that guide AI, not the ones replaced by it.

I have been reminded of this through my brilliant coworker LeeRon Yahalomi. Her simple reminders about how to communicate more effectively for change have been some of the most valuable lessons I've had lately. Not a big AI deployment. Just foundational communication. (Lil' appreciation mention for you on simple exchanges that have been really up-leveling/reminding me!)

So if you are wondering where to upskill right now, here is my take:
→ do not only chase the tools
→ invest in the thinking behind them

AI will make technical skills cheaper.
Clear thinkers and clear communicators will only become more rare.
& more valuable.

Great work doesn't speak for itself. It speaks through how you present it.
& that’s where the soft skills no one talks about come in.

We spend hours on LinkedIn trying to get better at our jobs:
→ What experiments should I run next?
→ What tweaks can I make to my ads?
→ What messaging frameworks are people using?

All helpful — but the quiet skills?
The ones that determine how your work is received, approved, and understood (& help you with internal politics)?
Those barely get mentioned.

Probably because:
1. No one loves acknowledging internal politics
2. These skills feel “too simple” (but even I need the "duh!" reminders)
3. Most don't like to say the quiet ladder climbing moves out loud 

These soft skills shape your career more than people realize.

Here’s one I had to remind myself of recently:
How you present your work matters. A lot.

You can check this as a recent experiment I did (as I know many want to hear about marketing experiments here!).

I was working on a big copy + messaging project (can’t share more yet 😉).
I knew this would spark a thoughtful discussion — which is a good thing, it means he’s invested in marketing.
But we're on a tight deadline, so I took a walk to think about how to collaborate on this better from my behalf, especially since we have a big time zone difference for actual collaboration.

So instead of dropping a raw Google Copy Doc, I redesigned the entire review experience in the Doc:

1. I led with context
I started with a section context as to what the project was and started with all the research: a Wynter messaging test, ICP insights, and a deep ChatGPT research dive he values. This is where knowing who you're presenting to and what they prefer matters, and I knew he valued research and data. Marketing can be very subjective and around taste, so this anchored it before we had differences in taste.

2. I explained my reasoning
Step-by-step thinking behind every angle and choice.

3. I visualized it
Figma mockups so he could see the copy in context — not floating on a page. I truly think work needs to be mocked up as so many have a hard time visualizing. 

4. I created a dedicated section for edits
This keeps feedback focused instead of everywhere. It was at the end of the doc so you had to go through the reasoning first.

Did I still get feedback? Of course.
But it was strategic, not subjective.
Refinement… not rewriting.

It reminded me of something a coworker once said:
“When I put work in a slide deck instead of a doc, I get fewer edits. It just looks more done. A doc signals that it's in draft mode.”

It sounds silly… but it’s true.
Aesthetics shape perception.
(Whether we love or hate to admit it)

So if you want smoother approvals, clearer conversations, and less chaos, try this:
→ Format your docs beautifully
→ Mock up your creative
→ Polish your slides
→ Tailor the presentation to how your reviewer thinks

Should I share more of these type of tips no one really talks about?

A client once asked me to 3x their paid media budget overnight. I said no.
Wild, I know. Especially coming from the person *overseeing* their paid.

Here’s the truth:
Most teams think about budget in tiny buckets… instead of one ecosystem.
Paid. Creative. Software. Headcount. Outside help.
It all ladders up to the same line item in the financial model. 

We get stuck in “program spend = paid channels.” This creates black and white thinking, instead of looking at it creatively to really make it work for you. 

When I looked at their data, two things were obvious:

1. Scaling spend that fast is risky 
You hit diminishing returns before you hit efficiency. It can also shock the system. You should scale overtime. 

2. They were trying to break into a new market, and weren't landing. 
Performance deep-dives showed the real issue wasn't just paid. 
It was messaging. They were speaking in a different market's pain. Pouring more spend on the wrong story just burns cash faster.

So instead of 3x-ing ads, I built them a spreadsheet of where to put the money. Most of which we didn’t own:
→ Channel diversity experimentation: podcast sponsorships to expand reach (move out of just LinkedIn/Meta/Google) 
→ Wynter messaging tests in a cascading order: homepage → demo page → product pages, etc. 
→ More creative variation 
(Side note: in general, the market focuses so much on the amount we spend on ads, but not on what we're actually paying to promote. That sounds SO silly, right?!) 

They ran with it. (One of my favorite clients ever. Not just because they listened 😉, I swear.)

The results?
 → A Wynter test results that the used to rewrite their H1 & H2 that improved homepage → demo conversions by 40% in the first 2 weeks. 

You could run so many hypothetical scenarios of what that impact is. Same amount of traffic, spend, etc., and your getting SO many more high-intent submissions. 

They didn’t deploy the budget in a “traditional” way.
 But it did exactly what they wanted: drive more results.
 And that’s the whole point of increasing paid spend in the first place.

This is why I'm more of a fan of reporting on marketing impact via Marketing CAC or on variable/program CAC. It allows marketing to become an ecosystem for the end goal you're trying to achieve. 

As we're all deep in 2026 planning, it's important to remember to think about the budget creatively, what it's meant for, and to not think in siloes.

’Tis the (planning) season — everyone’s buried in forecasts and spreadsheet math, wondering if we accidentally became full-time analysts overnight.
Pipeline targets. Budget models. The usual.

But there are a few non-numeric ingredients that quietly determine how strong your team operates next year — and they’re easy to overlook.

If you’re in planning mode, here are a few ideas worth considering (I know I am!): 

1. Building Space for Ongoing Learning
Skill growth doesn’t happen by accident. Planning for it ensures your team levels up in ways that compound over the year. You're being intentional vs. letting the workload take over. 

Potential goals:
→  Publish on LinkedIn X times
→  Guest on X podcasts
→  Build basic CRM reports
→  Deepen HubSpot/SFDC knowledge
→  Advance expertise in a specific craft area

2. Treating AI Execution as a Core Capability
AI is becoming part of day-to-day execution — not an optional add-on. But it takes time, reps, and structure to operationalize it well. We also can't expect employees to be AI-savvy without taking the time to teach them. 

Potential goals:
→  Each team member owns one AI workflow
→  Ship X new workflows each quarter
→  Monthly “AI learnings” or teardown sessions

3. Strengthening Product & Customer Knowledge
Everything gets sharper when marketers deeply understand what they’re marketing — and who they’re marketing to. Messaging. Content. Creativity. Decision-making. But not enough teams *truly* understand the product as deeply as our sales friends (brutal honesty here). 

Potential goals:
→  Listen to one sales demo per week
→  Everyone able to give a product demo by mid-year
→  Speak with X customers per quarter
→  Refresh ICP documentation 

4. Creating Room for Experimentation
Experimentation isn’t a culture that magically appears. It needs structure, expectations, and space to run.

Potential goals:
→  Launch X experiments by X quarter
→  Create a simple experiment template (these need to structured, and everyone deeply understands the importance of each piece (hypotheses, testing sizes, data, etc.) 
→  Build post-mortems into the process so you stack learnings from the experiments 

Annual planning will always revolve around numbers.
But the things that move those numbers?
They’re usually the pieces no spreadsheet can capture.

What “invisible” elements are you planning for this year?

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The Battle

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