#34 Interview series: From ClickUp Chaos to a Freelancer OS: Pricing, Positioning, and Finding Your Niche with Robyn Henke

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$100K Playbook with Mike Koziol

Mike Koziol

35 episodes

1 day ago

$100K Playbook is the no-fluff podcast for consultants and agency owners who want to scale smarter, earn more, and finally build a business that doesn't burn them out. Hosted by Mike, a former corporate lawyer turned 7-figure consultant, this show dives into the exact strategies, systems, and mindset shifts needed to grow to $100K months without bloated teams, endless client calls, or selling your soul to hustle culture. Each week, you'll get straight-talking solo/guest episodes, real-world case studies, and unfiltered insights on offers, pricing, lead gen, sales, and operational clarity.

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#34 Interview series: From ClickUp Chaos to a Freelancer OS: Pricing, Positioning, and Finding Your Niche with Robyn Henke

$100K Playbook with Mike Koziol

52 minutes 23 seconds

2 weeks ago

#34 Interview series: From ClickUp Chaos to a Freelancer OS: Pricing, Positioning, and Finding Your Niche with Robyn Henke

Welcome to the $100k Playbook with Mike Koziol

In this episode, I sit down with ClickUp consultant and longtime marketing freelancer, Robyn Henke, to unpack how freelancers can turn operational overwhelm into a scalable operating system. They cover why big, do-everything courses stall learner progress, how to reframe ClickUp as the vehicle (not the headline), and the power of niching by “who” and “what problem” to reduce education-heavy marketing.

Key topics:

Breaking a “too-big” course into an ascension model that drives completion
Why live cohorts boost accountability vs. self-paced (and why 95% never log in)
Pricing psychology: adding a zero, attracting committed clients, and cash flow
Positioning beyond tools: sell the “wake up in the morning” problem, deliver with ClickUp
Niching decisions: senior freelancers vs. agencies; problem-first messaging
Productizing and scope control to avoid scope creep and resentment
Validating offers fast: 30 discovery convos to test language and fit
Lead magnets that work: turning a PM tool buyer’s guide into list growth on LinkedIn
LinkedIn as a genuine networking channel for research, outreach, and hand-raiser posts

Timestamps:

00:00 Tech setup and recording switch
03:30 Robyn’s pivot: from marketing freelancer to ClickUp consulting/education
08:40 Course design lessons: simplify to essential steps
13:15 Live vs. self-paced and the 95% login problem
17:20 Pricing: why $2,500 beats $249 for outcomes and engagement
25:10 Niching: industry x problem, and aiming at “wake-up” pain
33:40 Don’t lead with tools; sell outcomes, deliver with ClickUp
41:05 Targeting agencies and productized offers to stop scope creep
49:30 Validating messaging with 30 quick conversations
56:10 Email list growth: the PM tools buyer’s guide and LinkedIn hand-raisers
1:04:00 Confidence, scope, and retainer structures for ClickUp implementations

Links/Resources:

Robyn’s weekly newsletter and YouTube (mentioned)
Idea: PM Tool Buyer’s Guide/Quiz as a lead magnet for LinkedIn
Concept: “Freelancer OS” framing with ClickUp as the implementation layer

Who this is for:

Senior freelancers/consultants feeling operationally underwater
Agencies struggling with onboarding efficiency and delivery chaos
Creators/course builders rethinking price, format, and positioning

Takeaway:Lead with the painful, urgent problem your ideal client wakes up thinking about. Package a tight, productized path to resolution. Use ClickUp as the engine—not the headline—and price for commitment and outcomes. Validation comes from real conversations, not waitlists.

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Connect with the host of the $100k Playbook Mike Koziol on Linkedin: https://www.linkedin.com/in/michalkoziol/

Download the 2025 Consulting report: https://mikekoziol.com/the-100k-consultant-report/

Download to $100k Offer Playbook: https://mikekoziol.com/the-100k-offer-playbook/

Schedule a free marketing brainstorming session: https://mikekoziol.com/connect/

Please rate the podcast on Spotify and iTunes <3

Tags: consulting, consultant, productization, scaling, service business, marketing agency, freelancing, fractional CxO, profitability, clickup