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2 weeks Upgrade Sprint with 

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Anastasia

Get a redesigned
upgrade journey 
in 2 weeks

In 2 weeks, you’ll see where users get stuck, why your current free-to-paid conversion isn’t there, and what the redesigned journey should look like.

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One of the new upgrade paths she suggested now converts about 3x better than what we had before, and we’ve also increased new trial signups.

Jason Pratts

CEO @ Kumo, DealStack.ai, Founder
of Appetize, sold to SpotOn for $415M

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We're now implementing her recommendations and working through the strategic decisions she helped us frame. The clarity we walked away with was well worth it.

Carlos Acosta Flores

Founder @ Pconnection.net

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Anastasia offered thoughtful ideas on everything from copywriting and flow to UX simplification and user psychology, all grounded in real-world startup experience.

Greg Weinstein

Founder & CEO at Audience Genomics

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Should you focus
on your upgrades?

Check all the points you can relate to.

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Let's solve your challenge
together 
 

2 weeks 

Upgrade Sprint

In 2 weeks, you’ll see where users get stuck, why your current free-to-paid conversion isn’t there, and what the redesigned journey should look like.

Pricing based on your size

(and the resulting complexity & impact)

Early, under $2M ARR

$5000

Growth, $2–5M ARR

$7,500

Scaling, $5M+ ARR

$9,000

What you'll get

An expert review of your upgrade journey

 

I go through the path from signup to payment the way a real user would, looking for confusion, missing value, weak triggers, and moments where users lose the reason to pay.

A data-backed diagnosis of what’s costing you revenue

 

I match the experience against your product data, funnel behavior, session recordings, and upgrade points to see where users drop, stall, or never understand the paid value.

A redesigned free-to-paid path

 

You get a prototype of redesigned upgrade moments your team can implement: from onboarding and paywalls to pricing pages, upgrade prompts, and in-product triggers.

60-min team walkthrough

 

I walk your team through everything live and answer any questions.

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Deliverable #1

Funnel Analysis

I look at where users drop, stall, or never reach the moment where paid feels worth it — matched against industry benchmarks to show you not just what's broken, but why users aren't making the decision to upgrade.

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Deliverable #2

Upgrade Journey
Breakdown

For every step from signup to upgrade trigger, I identify what users need to understand, feel, or believe before they're ready to pay — and where the current experience falls short of that. Each screen gets an insight, the gap between intended and actual user state, and the move that closes it.

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Deliverable #3

5-10
Redesigned Moves

Not a list of fixes. The actual redesigned product moments — prompts, paywalls, triggers, copy, flow — built around how people actually decide, ready to hand straight to your team.

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What will happen
step by step

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→ 

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Case Studies

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24% increase in trial-to-paid conversion
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x5 MRR Growth from PLG  Motion
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x2 free-to-paid conversion
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I’m Anastasia Kudrow

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10+ years

I’ve been helping digital products grow revenue for 10+ years

Simone Woods

Psychology-led

I use behavioral psychology to design around how people actually think, hesitate, decide, and pay.

Nicole Yang

0-$4M self-serve

I took my clients 0-$4M ARR in self-serve revenue in 3 years

Simone Woods

Leading PLG team

Work at leading PLG agency ProductLed with Wes Bush

Calvin Smith

Founder of Ghosted and PLG expert, deeply driven by psychology

Hear from my awesome

colleagues and clients 

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Productled

When our clients struggle with their free-to-paid conversion, Anastasia is the person I want in the room. She has a rare mix of psychology, product strategy, and ruthless prioritization - she can quickly pinpoint the real problem, even in noisy data and complex orgs, and turn it into concrete changes to onboarding, pricing, and upgrade flows. If you want to improve your free-to-paid conversion rate, working with her is an easy decision.

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Wes Bush

Author of Product-Led Growth,

Founder @ #1 PLG Agency ProductLed

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Productled

Anastasia is one of the very few people I trust to look at a messy funnel and tell me what actually matters. I’ve seen her handle very tough clients and teams, earn their trust fast with early growth wins, and still keep an eye on the long-term strategy. She combines deep user psychology with practical product sense, so her recommendations turn into clear, doable plans instead of vague insights.

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Rodrigo Fernandez

Chief ProductLed Implementer

@ Productled, ex-Time Doctor, ex-EOS

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BBC Maestro

Anastasia is an incredibly knowledgeable individual who offered advice on how to approach trials and freemium options for our brand.

She took the time to discuss the options we're exploring and shared pros, cons, and common pitfalls to watch out for.

She unlocked new concepts and considerations, which will prove invaluable as we progress through the validation stage. I'd highly recommend Anastasia as a mentor!

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Charlie Hamouy

Growth Marketer @ BBC Maestro

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Kumo

Anastasia worked with our team for a couple of months and helped us make real progress on free-to-paid conversion for our freemium product with a trial on top.
 
She set up product analytics so we could finally see how users onboard, where they drop, and where upgrades actually come from, then used that to guide changes to our trial model, pricing page, paywalls, and upgrade triggers. One of the new upgrade paths she suggested now converts about 3x better than what we had before, and we’ve also increased new trial signups.

Working with her was very easy. She combined clear strategic guidance with hands-on help: from designing the full event tracking system to producing mockups and real copy for the website and upgrade email flows.

I’d happily recommend Anastasia to any team that wants to improve free-to-paid conversion and build product-led upgrades growth.

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Jason Pratts

CEO @ Kumo, DealStack.ai,

Founder of Appetize, sold to SpotOn for $415M

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Aggie

Anastasia was incredible to work with — she brought clarity, structure, and empathy to a complex challenge. She quickly pinpointed the root cause of our user drop-off and helped me reframe what I thought were multiple issues into a single, solvable onboarding problem.

Her insights were both strategic and tactical, blending high-level frameworks with actionable, low-lift changes that will meaningfully improve user experience. She offered thoughtful ideas on everything from copywriting and flow to UX simplification and user psychology, all grounded in real-world startup experience. I left the session energized, reassured, and with a clear direction forward.

Highly recommend.

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Greg Weinstein

Founder & CEO at Audience Genomics

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Bridgemart

Anastasia was kind and extremely helpful. I felt that my concerns and issues were immediately understood, and I walked away with actionable feedback for both the short and long term. I came to the meeting wanting to better understand pricing strategy, and left with a plan as well as a new passion for finding creative ways to get user feedback on my product.

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Shay Longmate

Director @ Bridgemart

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MyLnker


I brought Anastasia in at a critical moment for MyLnker, a tool designed for entrepreneurs and content creators to optimize their online presence. We were facing a conversion challenge we couldn't fully diagnose internally users were signing up but very few were converting to paid. I needed an outside perspective from someone who understands how users think and why they don't upgrade.

Anastasia delivered a thorough audit of our full upgrade motion from onboarding to pricing to in-product triggers and came back with a clear, structured diagnosis and a prioritized set of recommendations. More importantly, she was direct. When I asked Anastasia the hard questions about our market and our model, she gave me honest answers grounded in data and real experience, not just what I wanted to hear. That kind of candor is rare and exactly what you need when you're making strategic decisions.

The live walkthrough session was particularly valuable. Anastasia walked us through real UX/UI observations, shared competitive references in real time, and helped us think through our priorities given our team size and stage.

We're now implementing her recommendations and working through the strategic decisions she helped us frame. It's a process, but the clarity we walked away with was well worth it.
 

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Carlos Acosta Flores

​Founder @ Pconnection.net

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Paper VPN

The Fastest Mind in the Wild West. Anastasia possesses a superb analytical approach, swiftly adapting to product changes, generating creative ideas, always staying connected, and exhibiting exceptional work capacity. I would hire Anastasia for any project I've been a part of.

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Dmitrii Sobolev

Head of Product @ Paper VPN

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Miro

As Anastasia’s Mentor, I've seen her work over the past year and I am impressed by her ability to turn ideas into real functioning products🚀

She's passionate about what she does, data-driven, and has a unique ability to get teams moving from planning to action. Anastasia's approach is both direct and supportive, fitting well with teams that value clear, effective guidance and a caring touch. Her skill in adapting to different team needs while focusing on common objectives is a great asset for startups aiming to grow and innovate!

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Viktoria Kharlamova

Growth Advisor, ex-Miro

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Join great teams with great results

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FAQ

Other questions?

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