Startup Underdogs Special Edition: Takeaways from DRIVE, Exit Five's In-Person Conference for the B2B Marketing Community

This week is a special edition for Startup Underdogs - last week I joined a small group of 200 B2B marketers in Burlington, VT to attend the first ever in-person event put on by the Exit Five team, DRIVE.

Exit Five has become the largest online B2B Marketing community where marketers go to network, share ideas, and help each-other grow their skillsets.

The line up of speakers was incredible and I took a ton of notes and thought they would make for a useful edition this week.

Indeed, some of the talks were not hyper relevant for the pre-PMF → PMF → initial scale phase many of us are living through; however, there are still plenty of takeaways and tactics you can start deploying today.

Note: Apologies in advance for some of the photos of the slides. If there's an image you can't see super well, feel free to message me and I can share a higher-res copy with you.

Top Takeaways for Early Stage SaaS Founders

• Create a "provocative POV" - come at your problem with a opinionated perspective on the problem (and solution).
• Tighten up your messaging and positioning. Help people understand what problem you solve, who you solve that for, and the impact of solving that problem.
• Content is the key part of your early-stage strategy. You won't have unlimited resources, which means you need to do better creating a system to produce high-quality content...and get it distributed.
• Who, and how, you hire reflects your Strategy. Read that again.
• Founder-led marketing on LinkedIn is thriving for B2B businesses. Be authentic. Be consistent.
• Events are in (particularly small niche events). COVID has left people craving authentic, in-person connection with their peers.
• Community marketing transforms brands, enabling a shift of marketing through, instead of to, your customers. Unlock your users/customers and turn them into brand advocates (and content creators).
• Bonus: I spent some time asking around on the effectiveness of outbound (calling and emailing). By and large, what I heard is: it's extremely effective when done well - for those saying it's dead, they are either unwilling to do the work, or simply not executing well.

Top Highlights from the Speakers:

• “Build the smallest marketing organization necessary”
• "When coming up with marketing ideas, run it through a simple framework “Is it unique? Is it valuable?”
• "Creating content is not a strategy. Create a highly authoritative piece of content with a provocative POV and distribute/remix it over and over."
• "There is massive opportunity in Reddit, graveyard Facebook pages, and niche newsletters."
• "Run more small events."
• "Everything can be measured through the lens of incremental growth."
• "Pick a word — earn mindshare to earn market share."
• "Content is the strategy; but, most businesses still don’t know how to create great content (or aren’t prioritizing it)."

How to Build a High Performing B2B Marketing Org - Peter Mahoney

My favorite comments:

• Build the smallest organization possible
• Align your team to your marketing strategy; if the strategy shifts, your team needs to shift
• Rule #1 for building a marketing org, make it simple: “If you can’t draw it on a napkin, you are doing something wrong”
• Resist layers
• Don’t design the org around any one individual
• Clearly define what is a service center and what is an outcome center

How to Say No to Your CEO and Leadership Team - Natalie Marcotullio

My favorite comments:

• Is it unique? Is is valuable? - When considering a new tactic or initiative get the entire team asking these questions to help vet the idea: Have I seen this done before in my industry? Can this be easily replicated by another company? Can our audience learn something from this? Will this help improve their day-to-day or career?
• People have turned into "serial skimmers". We need to match content to match the way they consume information.
• A framework is the best way to operate up to a CEO or Leadership Team, otherwise you are subject to "these are things we have to do" - you want instill that the current marketing initiatives are going to be done really well, and for many projects/ideas, it's not a never, it's just later.
• "After seeing the results, I firmly believe that a few core marketing areas thoughtfully chosen and executed well far outperform the broad range of marketing tasks that I assumed we just had to do (newsletters, webinars, etc)." - Navattic CEO

3 step-method for those needing to manage up:

• Why is this so urgent right now?
• Let's swap something out (deprioritize) to facilitate this work.
• Let's experiment with it - how can we try it with little budget or bandwidth (AND, outlining previous experiments and results)

Create Once, Distribute Forever: Content Marketing & Distribution - Ross Simmonds

My favorite comments:

• Creating content is not a strategy...you have to market it.
• Content needs to Educate (to build trust), Engage (to build community), Entertain (to build connection), and Empower (to build a tribe)
• The best content: how to do something, achieve something, address a problem you're trying to solve, is made provocative.
• Your approach is "SERP domination" - taking keywords and ensuring your brand, and content, is showing up everywhere.
• LLMs will have consumed everything by 2026...user generated content sites are next. Which means there is a window of opportunity to start building presence there.
• Be GREAT on one channel, don't be mediocre on all channels.
• "Message fatigue" is a lie. It works because people don't remember whatever it is you told them. You have to hit people with the message again and again and again (and on multiple channels).
• Content is the only way to do marketing.

Personal Note: I loved these 2 pictures and think every marketer, founder, and finance leader needs to sit and understand the complexity of the B2B buying process. If you are a first-time early stage B2B SaaS founder, it's exciting to launch your product, but this is the landscape you are staring down as you look to achieve PMF and scale your business. It's incredibly difficult and complex and navigate this all yourself.

The collage of slides is a little crazy, but I took a ton of pictures of Ross's presentation, it was so good!

Mission Possible: Measure Everything - Pranav Piyush

My favorite comments:

• Everything can be measured through the lens of incremental impact.
• Just because you can measure something doesn't mean you have to (or should).
• As you a brand you need to be physically and mentally available, which means: be present, be thought of, be physically available to buy something (search is physical availability on the internet).
• Social works the same way as TV, you don't click but it influences your buying experience.
• What people say and what people do are entirely different things - just because someone has said they have heard of a brand, there's no reason to imply they'd buy from you.
• If there's a complex sales cycle, attribution can be harder - it's important to match attribution to the things you can truly control; don't be afraid to set up two attribution models if there are variables that affect the model (product, solution engineers, etc).
• To effectively run incremental impact experiments, you need to design them so you're turning things slightly up and down to look for correlation to conversions.

Personal note: Everyone in the room agreed Attribution is still the #1 issue they were facing. I like the perspective of incremental impact. We spent MANY cycles at Cybrary trying to solve Attribution (not the way Pranav mentions, unfortunately) and came up with reports and dashboards that we didn't trust and never ended up impacting the business.

How to Build a B2B Community - Dan Cmejla

My favorite comments:

• Community marketing is the effort to place your customers as the primary distribution point for your brand - it enables a shift of marketing through, instead of to, your customers - it is identifying spaces of influence and deploying the customer voice to those spaces.
• Build paths from customer to advocate (and user generated content).
• Small community groups and events are working well right now.

LinkedIn for B2B Leaders - Devin Reed

My favorite comments:

• All-in on LinkedIn for B2B Marketing (some caveats)
• It's nearly impossible to take a strategy or a playbook and copy/paste them into an organization) -- that particular strategy or playbook worked at a certain time, for a certain product, for a certain audience.
• The best marketers (and consultants) can take frameworks, look at the strengths of the founders and the organization, and apply them to the business as it is today.
• I want people who influence and make buying decisions to: know who we are, like what we're about, and trust we can help them.
• Professional profiles get 5x more views than corporate pages - if you're focused on corporate pages, you're never going to win.
• You need to be focusing on building trust at scale, and trust is built person to person.

5 Step Process (notes)

Step 1: Pick your “one word”

What you want to be known for, what triggers people to talk about you, to earn mindshare…then you can win market share.

• If you’re not known for anything, or you’re known for the wrong thing…you won’t earn mindshare or you’ll get conversations about the wrong thing
• Consider Casual vs Closed Door conversations
• You’re “one word” is your content North Star

Step 2: Narrow your audience

Who is that one ideal person you want to come book a demo with you?

Step 3: Pick content pillars and topics

You're audience wants to know what you're seeing, thinking, and doing. What your audience cares about + your niche knowledge and experience = relevant and valuable content = content that converts.

Skill statements = I know how to...

Outcome statements = I know how to...

What's the most expensive problem?

What's the most urgent problem?

Step 4: Outline your production process

Great results come from processes, not promises. Commit (your CEO) to 3 posts/week from the content pillars for 90 days.

Tuesday: Idea and Brain Dump

Wednesday: Write 1st Drafts

Thursday: Revise Drafts

Friday: Finalize & Schedule

Step 5: Measure, communicate [what you're seeing], and iterate

Frameworks exist to help provide a structured approach to a problem, but the best talent knows to take observables and adapt the framework to drive success.

Additional Considerations:

• Dominate in your area
• Have a point of view (or people will tune you out) and a different approach
• Don't worry about saying the same thing as someone else, be differentiated by being yourself - the way you say it or do it, and your personality will make it different
• If you are doing this for a CEO or leadership team member, they need to be replying to comments (but you can't force them to).
• Maintaining voice and tone are key - the Thursday draft revision days are the chance to do this. Bonus: After a little time, you can train an LLM to streamline this process.

AI-Powered $0 CAC Strategy - Kyle Coleman

My favorite comments:

• Content is the strategy, but most companies have bad content.
• Provocative POV - paint a vision for a different future, architect the "from/to" journey.
• During his interview, Kyle took 4 screenshots of competitors (1 being his company) to showcase the lack of identity each had. This is the basis of needing an identity, a provocative POV.
• Example, Copy.AI came up with their own category GTM AI and own term "GTM Bloat"; building a narrative around the accumulation of resources to support GTM that are underdelivering and under performing, and if solved, will enable you to run a successful company and achieve real, sustainable success.
• Not being known for anything (or being known for the wrong thing), won't earn you mindshare - or you'll get into the wrong conversations - and without mindshare you can't capture market share. Consider casual conversations and closed door conversations, you want that trigger "word" to lead to associated mindshare. Your goal is to define the trigger word, associate yourself with it, and strategically drive casual and closed door conversations to trigger that in conversation.

Start with this:

• What problem do we solve?
• Who we solve that for?
• What is the impact of solving that problem?

Next, build a content operation:

• Thought-leadership (real thoughts from real SMEs)
• Product user cases (real use cases from real SMEs)
• SEO optimized (harness the power of the internet to distribute)

Then, lean into the demand flywheel:

• Content → Web Traffic → Conversion Points → Inbound Leads → Demos → Transcripts → Content

That's a wrap!

After nearly 10 years of being heads-down at Cybrary, it was refreshing to get out and learn from others in the industry. It validated a few things for me:

• We were way ahead of the market during the early years - creating a provocative POV, growing through our community, and building a content engine at scale.
• Attribution is still a pain in the a** to solve for (though every finance leader and career-VC is going to continue to waste cycles pushing companies to define it anyway).
• We fell way behind the market in the later years of the business. There are a lot of talented B2B marketers out there, but for startups it is really hard to hire people right-sized for your business.
• If you're a founder or early team member, don't wait to start the process of building your personal brand in tandem with your startup. It's something I wish I invested more into while building Cybrary. I know what you're thinking "I don't have time for that with everything else I need to do to keep this business alive". I'll repeat the statement from above, personal profiles get 5x more views than company pages...and, people buy from people. Talk about the challenges of building your business, what the market has wrong about current solutions, and your opinionated point-of-view of the way your problem should be solved. Become a trusted digital resource for your tribe.
• As founders and early stage company builders, it's valuable to take the time to go out and connect with our peers. At the very least, don't underestimate the value of working with advisors and consultants. Continue to get a lay of the land into what's working and why for other businesses, but understand everything needs to be adapted for your business.

Final note: All of these marketing strategies, tactics, and frameworks are wonderful in theory, but conceptually they are all just ideas. And ideas are worthless without exceptional execution.