Fractional SaaS Advisory · AI-powered

Connecting product, finance,
and GTM into one growth system.

17 years of SaaS operator experience — instantly accessible, powered by AI, and backed by a human when it counts.

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17+
Years in SaaS, from $25M to $1B ARR
3
Engagement tiers — self-serve to embedded
24h
Response time on flagged questions
Borthwick Advisory / Strategy Q&A
Advisory Access
Company Context optional but improves answers
We sell indie games — 100+ titles, 3,000 subs at $5/month.
Your Question
How can we double size in the next 12 months?
How do I price a freemium tier?
Moving upmarket — GTM changes?
Board narrative around ARR expansion?
Get answer
Responses in ~10 seconds
Advisory Response
Context
You're running a subscription gaming bundle — think Humble Choice or Xbox Game Pass Indie tier — and the question is really about which growth levers matter most at 3,000 subscribers before you burn money on the wrong ones.
The Answer
At 3,000 subs and $5/month, you're at ~$180K ARR. Doubling means getting to 6,000 subs or finding ways to expand revenue per subscriber — ideally both. Fix retention first, then add annual plans, then launch a referral loop...
Companies Jon has worked with
Toast GoTo LogMeIn LastPass Rapid7 Jive
The Problem

Growth-stage SaaS is stuck
between two bad options.

The alternatives
  • Junior consultants produce frameworks, not decisions
  • Full-time VP hires cost $250K+ and take 6 months to ramp
  • Agencies are generalists — not SaaS pricing operators
  • AI tools have no institutional knowledge of your market
  • Board decks don't connect to operational reality
Borthwick Advisory
  • 17 years of SaaS operator experience baked into every answer
  • Available instantly — no hiring process, no ramp time
  • Specific, quantified answers built for actual use
  • Complex questions escalated to Jon directly — reviewed within 24 hours
  • Pricing, GTM, and board narrative in one relationship
How It Works

Ask anything. Get an operator's answer.

The advisory is powered by AI trained on 17+ years of SaaS pricing, GTM, and product strategy — with Jon in the loop on what matters.

1
Ask your question
Type in any pricing, GTM, or strategy question — packaging decisions, competitive positioning, board prep, segmentation. No scheduling, no waiting.
2
Get an operator's answer
The AI draws on Jon's SaaS experience — LogMeIn at scale, Cordance acquisitions, Rapid7 commercial strategy — to give you a specific, actionable response. Not a framework. An answer.
3
Jon reviews what matters
Complex or high-stakes questions get flagged for Jon's personal review. He looks at them daily and sends back a direct answer — often within a few hours. You're never just talking to a bot on the hard stuff.
What People Ask

Real questions. Operator answers.

The kinds of questions growth-stage SaaS teams face every week — and can't get a straight answer on.

We're thinking about adding a usage-based tier. How do we price it without cannibalizing our seat-based customers?
Instantly surfaced from Jon's experience running hybrid pricing at LogMeIn and Cordance — with specific guardrails on floor pricing and grandfathering logic.
Our board wants a competitive moat slide. We have real differentiation but can't articulate it without sounding generic.
Worked through interactively, with Jon's direct feedback on board narrative that connects to financial outcomes — not just product features.
We're entering enterprise. What changes in the GTM motion when we go upmarket from SMB?
A detailed answer from operator experience — not a "land and expand" slide deck. Specific guidance on champion identification, procurement cycles, and proof-of-concept structure.
We just got acquired. How do we protect our pricing during integration without losing customers?
Jon led pricing through 10 acquisitions at Cordance ($0 to $40M ARR in 18 months). This is exactly the kind of question that gets escalated to him directly.
See It In Action

A real question. A real answer.

This is actual output from the advisory — unedited. The question came from an indie gaming subscription company with 3,000 subscribers.

Company Context Optional but improves answers
We sell indie games — over 100 titles, 3,000 subscribers, $5/month.
The Question
How can we double size in the next 12 months?
Advisory Response
Copy New question
Context
You're running a subscription gaming bundle — think Humble Choice or Xbox Game Pass Indie tier — and the question is really about which growth levers matter most at 3,000 subscribers before you burn money on the wrong ones.
The Answer

At 3,000 subs and $5/month, you're at ~$180K ARR. Doubling means getting to 6,000 subs or finding ways to expand revenue per subscriber — ideally both. Here's how I'd prioritize:

1. Fix retention before pouring water into a leaky bucket
Before any acquisition spend, know your monthly churn rate. At this scale, even 8% monthly churn means you're replacing nearly your entire subscriber base every year just to stay flat. Target under 5% monthly. Retention is your growth multiplier — every point you save compounds.
2. Add a second price point — annual plans
Offer an annual plan at $45–48/year (20–25% discount). This does three things: drops monthly churn to near zero for that cohort, pulls cash forward, and signals commitment from your best customers. Even if only 20% of new subs take annual, your blended churn profile improves materially. This is the single highest-ROI pricing move at your stage.
3. Launch a referral loop
Your existing 3,000 subs are your cheapest acquisition channel and you're almost certainly not using them. Give subscribers a unique link — one free month for them, first month free or discounted for the referred friend. Gaming audiences are tribal. A 10% referral conversion rate on your base generates 300 new subs with near-zero CAC.
Priority Order for Next 90 Days
1. Know your churn rate  ·  2. Launch annual plans  ·  3. Launch referral program  ·  4. Test one distribution partnership
One Thing to Pressure-Test
Do you have licensing rights that allow you to bundle and distribute these 100+ games in a subscription model, and are those rights exclusive enough to defend against a larger player replicating your catalog? Your catalog relationships are your moat; make sure they're contractually solid before you scale acquisition aggressively.
— Borthwick Advisory
⚑ Flag for Jon's review Complex or high-stakes? Jon will respond within 24 hours.
Pricing

Start instantly. Escalate when you need to.

Three tiers — built around how much direct access to Jon your situation actually requires.

Free
Try one question, no account required. See the quality before you commit.
Ask a free question →
Self-Serve
$149/mo
Cancel anytime
Unlimited access to the AI-powered advisory, trained on Jon's SaaS experience. Instant answers on pricing, GTM, and strategy — no scheduling required.
  • 50 questions per month included
  • Additional questions $2 each, billed at period end
  • AI answers trained on 17+ years of SaaS operator experience
  • Pricing, GTM, segmentation, board narrative
  • Response in seconds, not days
  • Cancel anytime, no commitment
Get started
Most popular
Guided
$499/mo
Month-to-month
Everything in Self-Serve, plus your most complex and high-stakes questions get flagged for Jon's personal review — answered directly within 24 hours.
  • 250 questions per month included
  • Additional questions $2 each, billed at period end
  • Complex questions flagged to Jon automatically
  • Jon's personal responses within 24 hours
  • Monthly 30-min strategy call
  • Direct email access for urgent issues
Get started
Early access
Connected
$2,499/mo
Month-to-month
The advisory, connected to your Salesforce. Ask any pricing or GTM question — the AI reads your pipeline, ARR, and segment data live and answers from Jon's playbook against your actual numbers.
  • 500 questions per month included
  • Additional questions $2 each, billed at period end
  • Live Salesforce data — pipeline, ARR, segment mix, churn signals
  • Answers grounded in your numbers, not hypotheticals
  • Complex questions flagged to Jon within 24 hours
  • You hold your own credentials — we touch nothing
Embedded
By application
Limited availability
Jon embedded as a fractional operator — CMO, CPO, Head of Pricing, or VP Strategy. For companies that need an operator in the room, not just an advisor in their inbox.
  • Everything in Guided
  • Jon's direct time — 2 to 3 days per week
  • Full team and stakeholder access
  • Board and exec prep included
  • 3-month minimum, structured handoff
Connected Tier

The advisor, connected to your data.

Most advisory is hypothetical. Connected isn't. The AI reads your actual Salesforce data — pipeline, ARR by segment, churn signals, deal velocity — and Jon's pricing and GTM playbook runs against your numbers, not a generic SaaS model.

Without Connected
  • "Our enterprise pipeline is strong" — but no one can quantify what strong means
  • Pricing advice built on your description of the data, not the data itself
  • Segment analysis done by hand before every conversation
  • Questions answered in the abstract — useful, but not actionable this week
With Connected
  • Ask "which segment is churning fastest?" — the AI queries Salesforce and answers in seconds
  • ARR expansion analysis built from your actual account records
  • Pipeline coverage ratios and deal velocity calculated live
  • Pricing decisions grounded in your real segment economics

Salesforce at launch. Additional MCP integrations (HubSpot, Chargebee, Snowflake) on the roadmap.

Join the waitlist →
Connected in Action

Five questions that change when
the advisor has live data.

These are the kinds of questions Connected answers in seconds — not because the AI is smarter, but because it's reading from your actual Salesforce records, not a hypothetical.

Which of our pricing tiers is churning fastest, and is it structural or recent?
Connected queries closed-lost and churned accounts by product tier across the last 12 months, compares churn rate by cohort, and flags whether it's accelerating. Answer in ~8 seconds. Without live data: you'd need to pull this manually before you could even ask the question.
We're raising prices next quarter. Which accounts are most likely to push back based on deal history?
Connected pulls discount history, negotiation notes, and contract end dates across your Salesforce accounts. Surfaces the top 20% by churn risk before you start the conversation. Jon's frameworks on price-increase sequencing run against your actual account list — not a template.
Our pipeline coverage looks healthy but close rates are dropping. Where's the break?
Connected calculates pipeline coverage ratio by stage, close rate trends by rep and segment, and average deal velocity over the last 90 days. Cross-references against stage distribution changes. Most pipeline coverage problems are actually late-stage concentration — Connected shows you which one you're dealing with.
What's our net revenue retention by segment, and which segment has the best expansion economics?
Connected queries ARR by account at the start and end of each period, calculates NRR by segment, and ranks segments by expansion rate. Surfaces the segments where your upsell motion is working versus where you're bleeding quietly. NRR by segment is the highest-signal number most teams are flying blind on.
We just ran a discount-heavy quarter to hit the number. What did that actually cost us in ARR?
Connected calculates the difference between contract value at list versus contract value at close across the quarter, computes the ARR impact of average discount depth, and projects the compounding cost at renewal. Jon's view: discounting to hit a number is borrowing from your next quarter at a variable interest rate. Connected shows you the rate.
Join the Connected waitlist →
About

The connective tissue
between functions.

Jon Borthwick has spent 17+ years inside high-growth SaaS companies — not advising from the outside, but running pricing, GTM, and commercial strategy as a senior operator. His edge is the connective tissue between functions: turning product, finance, and go-to-market into a unified growth system.

At LogMeIn, he spent 13 years scaling from $25M to $1B ARR — leading pricing strategy on the GoTo merger (tripling ARR overnight), driving the $125M LastPass acquisition, and growing LastPass ARR from $12M to $40M post-close. At Cordance, he was Employee #4 — building the commercial model for a PE-backed SaaS roll-up that went from $0 to $40M ARR in 18 months across 10 acquisitions, including migrating an entire portfolio from perpetual licenses to SaaS. At Rapid7, he led monetization strategy, platform packaging, and ARR uplift for a publicly traded MDR provider.

The advisory is built on that experience — compressed into an AI that can answer most questions instantly, with Jon in the loop on everything that actually matters.

Progress Software
Director, Pricing Strategy
Current · Publicly traded infrastructure SaaS
Rapid7
Sr. Director, Commercial Strategy
Publicly traded MDR & cybersecurity
Cordance
VP Pricing & Product Marketing
Employee #4 · $0 → $40M ARR · 10 acquisitions
LogMeIn
VP Business Strategy & Operations
13 years · $25M → $1B ARR · LastPass acquisition · GoTo merger
Toast
Independent Pricing Advisor
Growth-stage SaaS advisory

The question you can't get a straight answer on — ask it.

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jonborthwick@gmail.com · Boston, MA · borthwickadvisory.com