DemandLoops

Soloprenuer

Thoropass

Fractional VP of Marketing

Fractional Head of Growth

Clay

Content Creator

UserEvidence

UserEvidence automates social proof for GTM teams. Generate verified customer evidence, product stats, and ROI data in minutes. Game-changing B2B companies like Pendo, Workato, Gong, Jasper.ai, and Ramp rely on UserEvidence to boost buyer confidence, shorten sales cycles, and increase win rates.

Advisor

Refine Labs

VP of Marketing

Chili Piper

Chili Piper is the most advanced routing and scheduling software for B2B revenue teams. 
We solve interesting problems, live and breathe our core value of “help,” and have a ton of fun doing it while fully distributed around the world — powered by espresso and hot sauce.

Senior Director, Demand Generation

brightwheel

Interim Head of Demand Gen

Interimly

In my time at Interimly I helped brands like Vanta, Anvyl, Honeycomb.io, Traackr, Mux, and Spoke.ai develop their demand gen and marketing operations foundations and programs for scale.

Demand Gen Consultant

Campaign Monitor

CM Group is a family of global marketing technology brands founded in 2017 with the collection of three industry-leading email marketing platforms: Campaign Monitor, Delivra and Emma. Since then, our family of brands has grown with the addition of Liveclicker and Sailthru in 2018. As CM Group continues to grow, this suite of products is changing the marketing landscape and presenting new opportunities for businesses around the world.

Head of Demand Generation

Demand Generation Manager

Kindful

Solving demand gen headaches ➿

Hi, I’m Kaylee 👋 founder of DemandLoops.

I’m the marketing solopreneur making demand loops a reality for B2B SaaS companies. After spending years in-house building and leading demand gen functions one brand at a time, I’m now going solo to bring my learnings to you.

I spend my days doing 3 things:

1. Fractional Marketing Leadership roles in B2B startups to help them build and scale.

2. Advising early and growth-stage founders and marketers on demand gen strategy.

3. Writing, creating, and talking about 1 + 2. 

I’ve operated and advised companies such as Kindful, Campaign Monitor, Chili Piper, brightwheel, Refine Labs, Vanta, Traackr, Mux, and many more. And am now trying to make my own newsletter happen fueled by my learnings – DemandLoops.substack.com 📧 I love helping others further their career in demand gen, while also continuing to push and define the boundaries of what this function will become. 💙

_____________

✌️ Areas of expertise: Demand generation, brand marketing, community, podcasting, performance marketing, marketing analytics, marketing operations, influencer marketing, field/event marketing, customer marketing

🙅‍♀️ Areas you won't catch me in: SEO, display advertising, lead gen

Kaylee Edmondson

Babe, are you ok? 

I've seen your ads 100 times now and still couldn't tell what the software does.

This company spent $200K on AI tools last year while their CRM had 47,000 duplicate records.

Their marketing automation platform couldn't talk to their data warehouse. 
Three different definitions of "qualified" lived in three different systems. 
Sales didn't trust any data coming from marketing.

But, don't worry, they hired a prompt engineer. 🙄

The same pattern keeps showing up in audits. Companies stack AI tools on top of infrastructure that barely worked before. Clay for enrichment. 6sense for intent. Pocus for intent/more enrichment. Custom GPT implementations. Multiple AI-powered ad platforms.

Their VP of Marketing said something that stuck: "We have all this data, but we're less confident in our targeting than we were two years ago when we had a simple scoring model in HubSpot."

Accounts with 4-7 duplicate entries because different tools were creating records differently. Intent signals weren't syncing with HubSpot. Product usage scores lived in a completely different system than their MQLs. 

When sales asked "why is this account qualified?" marketing couldn't answer because the signals were scattered across too many places.

AI doesn't fix bad data. AI scales bad data.

Your fancy AI tools are only as good as the foundation they're built on. 
Most B2B companies have duplicate accounts, fragmented contact records, inconsistent taxonomies, and disconnected systems. Then they wonder why their AI initiatives feel like expensive chaos.

The companies seeing real results spent the last year doing the work nobody wants to talk about. 

Cleaning their data model. 
Connecting their systems. 
Building operational processes. 
Investing in RevOps capacity. 
Saying no to shiny tools until they fixed their foundation.

The hardest conversation in B2B right now: telling leadership the answer isn't another AI purchase. The answer is a few months of unglamorous data work that nobody wants to fund or celebrate.

But that unsexy infrastructure work pays off. Every 👏 single 👏 time 👏

I almost didn't send the DM to Elena Verna.

Sitting there in 2023, cursor blinking in the message box, thinking "why would she respond to me?"

But I was stuck. Full-time marketing role, great salary, and this nagging feeling that going solo was the move—but zero confidence to actually do it.

So I sent it. Cold DM. Asked for a chance to talk about her career path and going independent.

She said yes.

That conversation gave me three things I couldn't get anywhere else:
- She told me the specific early learnings she made going solo (I copied all of them).
- She validated that my skill set was enough—I didn't need another certification or title first.
- She showed me what was possible. Seeing someone I respected who'd done it made it feel real, not reckless.

Three months later, I went solo. Built DemandLoops.

Looking back, that DM was the highest-ROI 45 seconds I've ever spent on my career.

The pattern I've noticed since: the person you're intimidated to reach out to is often the exact person you need to talk to.

They've been where you are. They remember what it felt like.
Most will say yes if you're genuine about why you're asking.

I still take 2 cold networking calls a month because that Elena conversation showed me how much faster you learn when you just ask someone who's ahead of you.

Last week someone cold DM'd me about going solo. We talked for an hour. I hope it helps them the way Elena helped me.

So...who's your Elena? The person you keep thinking about reaching out to but haven't yet? Today's the day. 🫶

Harness & Hone

Harness & Hone is a Digital Consulting Accelerator that has taught dozens of service-based Solopreneurs how to package their core competency into a repeatable, sellable, scalable business.

Unlike other programs, you won't just get advice -- you'll start selling a codified offer in 90 days, shift your business from deliverables to outcomes, and graduate with a level of personal income you've never thought possible.

Founder

1,000 Routes

Join me every week as I explore the stories, learn the lessons, and track the uncommon routes that common Solopreneurs take to get more clients, earn more money, and plant their flag.

Founder & Host

IMPACT

As a creator and member of the marketing leadership team, my main challenge was to create and scale net-new revenue programs to maturity and iterate and improve on existing ones. 

My focus is on creating content programs that truly resonate with our target audience. Guided by qualitative audience and customer research, my aim is to engage them in a way that keeps them coming back for more, whether it's attending events, listening to podcasts, or sharing our content with their peers, we can build a loyal and dedicated following that will support our business for years to come.

Setting the vision and strategy, our challenge was to move internal subject matter experts into leading, well-known thinkers within the sales and marketing category.  

Using a category lens, I guided the creation, refinement, and distribution of IMPACT's category POV and intellectual property. Through our SMEs, we intentionally moved our problem<>solution framing, languaging, and messaging into the marketplace. Primary internal and external channels include podcasts, newsletters, publications, YouTube, and social media.

Responsible for generating Stage 2 pipeline and achieving revenue targets for the Mastery business unit,  as well as all revenue and marketing operations.

Director of Demand

I created the content, campaigns, lead generation strategy, and sales process needed to accelerate the referral and event partner program growth.

I executed joint marketing campaigns for partners (e.g, sponsor booths, courses, promotional videos, speaking engagements, blogs, email, webinars, etc.) in collaboration with our video production team, content manager, and web designer.  Worked with partner teams to develop, plan and execute sales initiatives resulting in 356% revenue growth.

Account Executive, Partnerships & Events

As a HubSpot Certified Trainer, I provided ongoing tool support and training for sales, marketing, and leadership teams for all HubSpot hubs. This includes ongoing 1:1 and 1:many training and workshop sessions. Consistently staying up to date on new features and best practices.

Additionally, I created and executed on inbound sales and marketing strategies for up to 12 clients simultaneously.

HubSpot Enablement Specialist & Inbound Marketing Strategist

Verizon

During my time as a Solutions Specialist, I continually exceeded my monthly sales targets for all mission-critical KPIs including net-new sales, customer renewals, and revenue per transaction.

My core responsibility was to create personalized hardware and software solutions for all customers, B2B and B2C.

Awarded as the #10 salesperson in the New England area. Additionally, I created a peer-to-peer recognition program which was adopted as a standard throughout the region.

Solutions Specialist

Overcome the perception of being a generic, cookie-cutter agency

Most Solopreneurs face the same problems. 

They can’t tell you what they do or how they do it. 

It's taking longer, it's been harder, and most of the time you're picking up clients that aren't a great fit.

You have enough to get by, but you can't say you're successful.

It's kind of a grind.

And if you continue to work the offer you have, **nothing will ever change.**

You know you need a change, but are not sure how to do it **without risking your current customers who are paying the bills.**

Leaving so many talented Solopreneurs questioning why they even started a business in the first place.

The truth is you can’t outwork this problem. With your current offer, more of the same clients will bury you in work, and most won't pay you what you're worth.

Harness & Hone solves that problem. We give you the structured guidance you need to design a service that leverages what you do best, creates tangible value for your clients, and charges for the outcomes you produce.

Nick Bennett

Most solopreneurs frame their offer (and the problem they solve) through a buyer's failure.

"Your pipeline is empty."
"You're struggling to close deals."
"You don't know what to do next."

And they wonder why they only attract desperate buyers with shallow pockets.

I learned this lesson the hard way when I first started helping solopreneurs. 

I tried to hard to articulate a visceral, painful problem.

The response? Tons of engagement from people who needed a parachute.

I saw similar patterns across a few clients, too.

So we reframed the offer (and problem) around a buyer's success.

Suddenly, the quality of conversations changed completely.

→ From failure indicator: "Your website gets no traffic" 
→ To success indicator: "Your website gets 50K visitors/month, but you're only converting 1% when industry leaders in your space are at 3-5%"

→ From failure indicator: "Nobody knows who you are" 
→ To success indicator: "You have strong brand recognition in your niche, but you're struggling to break into the enterprise segment where deals are 10x larger"

→ From failure indicator: "Your sales team keeps missing quota" 
→ To success indicator: "Your sales team is hitting quota, but you're leaving money on the table because your top performers can't scale their approach to the rest of the team"

→ From failure indicator: "You can't afford to hire more salespeople" 
→ To success indicator: "You're profitable enough to expand your team, but you need a system that ensures new hires ramp as fast as your best rep did"

→ From failure indicator: "Your marketing isn't generating any ROI" 
→ To success indicator: "Your marketing generates consistent ROI, but you're capped at your current spend level and can't scale profitably past $X/month"

→ From failure indicator: "You can't deliver on time" 
→ To success indicator: "You're delivering on time, but manual processes mean you can only handle 20 clients when demand exists for 100+"

The difference is simple, but it makes a massive difference in your marketing effectiveness and pipeline strength.

Failure indicators attract people looking for a parachute. 

Success indicators attract people looking for partners.

When you frame through failure, you're fishing in shallow water. 

You get buyers who need all the help in the world but can't really afford it. 

They're trying to stop the bleeding, not build something better.

When you frame through success, you're fishing where the big fish swim. You get buyers who have already proven they can execute. 

They have the means to invest because they've already seen returns.

One frame brings you clients who haggle over every dollar. 

The other brings you clients who ask, "When can we start?"

Most solopreneurs never realize they're filtering their pipeline with their first sentence.

#plantyourflag

Nick Bennett 🏴‍☠️

Digital offer and content creation for scaling solopreneurs | Co-Founder @ Duo

Most solopreneurs never ask themselves, "What am I building toward?"

They just work to the end of the week, wake up on Monday, and do it again.

Getting through the week is the "plan."

And you feel like you're living the same day, over and over and over again.

One day, they wake up and realize they overlooked one of the most important questions in business.

But if it's so important, why do most solopreneurs skip it entirely?

Because casting a vision feels indulgent, impractical, too "woo-woo," or too overwhelming. 

You've got clients to serve, content to create, and revenue to generate. 

You don't have time to sit around pondering your ideal life when there are deadlines to hit.

Plus, the conventional business wisdom is clear: focus on the metrics. 

Revenue, growth, and scale matter most. Vision is something you figure out later, once you've "made it."

Except that's exactly backwards.

Success doesn't magically cure your limiting beliefs. 

It exposes them.

And it usually leads to a point where you wonder, "Is this what I actually want?"

It's easy to put off vision work because it's confronting and challenging. 

But if you want to escape Groundhog Day, chart a course beyond the end of the week.

#plantyourflag

Most solopreneurs get stuck in the Recognition Gap because they haven’t made a clear decision about what they want to be known for. 

They rely on word of mouth, custom-scope every project, and try to grow a business without ever getting anchored to the one thing they do best.

In our experience, this happens because we’re scared. 

Scared of prospects thinking we can’t do more than advertised. 

Scared of losing hard-won skills to atrophy. 

Scared of being seen as unable or unwilling to solve versatile problems.

The result is a business that evaporates the moment referrals slow down.

Worst of all, most referrals come in ice cold without context for who you are, how you think, or what problem you solve.

(Not ideal when you're trying to standardize what you do.)

But they do bring in money, which is why too many solopreneurs miss the Recognition Gap signs:

→ You can’t articulate what problem you solve (or who it’s for) in a clear and consistent way

→ Most of your work comes from referrals, and the few cold inbounds seem like miracles

→ You dread when a client leaves because you realize there’s no process to backfill clients

If nobody beyond your bubble knows what you do—or how you think—you don’t have a sustainable business.

Being good at what you do is required; it isn’t enough to hedge against risk.

If your only marketing channel is “people who already know me," your business is one slow season away from chaos. 

That's incredibly stressful. 

And it's why you can be at $20K, $30K, even $50K+ months and still feel like your business could evaporate overnight.

It’s deceiving because you’re busy, making good money, and are excellent at your work. Until one day you look up and…

Panic.

#plantyourflag

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The Battle

Kaylee Edmondson

Nick Bennett

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The Battle

Kaylee Edmondson

Nick Bennett

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Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Kaylee Edmondson's LinkedIn Performance

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