# Jonathan Boston

Jonathan Boston advises B2B companies and private-equity teams on commercial structure: how sales roles, processes, forecasting, and incentives work together to make revenue more predictable.

- Profile: https://b2binfluencer.marketing/creators/jonathan-boston/
- LinkedIn: https://www.linkedin.com/in/jmboston
- LinkedIn followers: 3,821
- Median of last 7 posts: 2 reactions, 0 comments (checked 2026-11-02)
- Topics: sales, revenue-operations, sales-forecasting
- Based on 10 dated posts, latest 2026-08-28

## Summary

Most useful for diagnosing B2B commercial structure before hiring a CRO or changing tools.

- Best for: A PE-backed or founder-led B2B software or services company with an untrusted forecast.
- Not for: Consumer or direct-to-consumer sponsored-placement campaigns seeking paid posts and broad reach.
- Check first: Confirm whether they offer sponsored placements and any audience data for your brief.

### Takeaways

- Unpredictable revenue may reflect commercial structure, not a weak salesperson or faulty CRM.
- One salesperson may handle prospecting, closing, and renewals while no one owns expansion.
- Most $40M to $300M B2B companies have a structure problem, not a talent problem.

## Main ideas

- **The problem is usually the commercial structure, not the people**: Boston's central claim is that unpredictable bookings at $40M–$300M B2B companies usually come from how selling is organised: which roles exist, who owns expansion, what the pipeline stages measure, and what incentives reward. The faults are easy to miss because nothing breaks visibly until a board meeting forces a forecast conversation. The reasoning runs that structure decides whether individual effort compounds into repeatable revenue, so swapping people without changing structure leaves the same gaps in place.
- **Run a diagnostic before hiring a CRO or reshuffling leadership**: Boston argues that companies decide a chief revenue officer is the fix before they have diagnosed what is broken, when the problem often sits in the process underneath the role. A structured, evidence-based commercial diagnostic is presented as the way to separate leadership gaps from process breakdowns, define the role precisely, and target the right profile. The point is about sequencing rather than avoiding senior hires.
- **Forecast reliability is an operating system, not a target**: When revenue targets outpace the systems supporting them, Boston argues that growth stops being an outcome and becomes luck. The fix described is commercial architecture: repeatable rhythms across pipeline, forecasting, and accountability, plus cleaner pipeline hygiene, more reliable forecasts, and team-level KPIs. A new sales leader or another push for deals is treated as a substitute for that work rather than a solution to it.
- **Commercial structure as a value-creation lever in private-equity ownership**: Boston positions commercial structure as a valuation lever rather than an administrative exercise, aimed at private-equity operating partners and founder-CEOs. The argument is that transitions such as a raise, exit, integration, or leadership change expose whether revenue systems can hold up, so structure work belongs in the value-creation plan alongside the operating plan. The levers named include organisation design, cross-functional alignment across sales, marketing, and customer success, pricing, and incentive design.

## Work to read

- [Why your board stopped trusting the forecast](https://www.linkedin.com/posts/jmboston_forecast-activity-7496261720508776448-aBCd)
- [Most $40M–$300M B2B companies have a structure problem, not a talent problem](https://www.linkedin.com/posts/jmboston_privateequity-b2bsaas-revenueoperations-activity-7521263284424052737-LZbb)
- [A mis-hired CRO can cost more than $1 million](https://www.linkedin.com/posts/jmboston_privateequity-b2bsaas-revenueoperations-activity-7521620882952278016-QWQN)
- [Run a commercial diagnostic before hiring or reshuffling a CRO](https://www.linkedin.com/posts/jmboston_privateequity-gtm-revenueleadership-activity-7521608118619791360-1wBf)
- [Commercial-structure levers for $40M–$300M B2B companies](https://www.linkedin.com/posts/jmboston_diagnose-your-commercial-structure-before-activity-7523054113966698496-5MJR)
- [When revenue targets outpace the systems that support them](https://www.linkedin.com/posts/jmboston_privateequity-saas-revenueoperations-activity-7520515880070348814-RAcf)

## Partnerships

The reviewed LinkedIn posts from Jonathan Boston are commentary and article promotion on commercial structure, revenue operations, forecasting, and CRO hiring, not a sponsorship program. Across all twelve posts there is no rate card, media kit, audience-deliverable specification, sponsored-format description, or partnership inquiry route. Each post either links to a longer article Boston wrote or invites a conversation about advisory work, which is a buyer-side consulting offer rather than a paid placement option for a brand. Because no partnership terms are documented in the reviewed material, there is nothing here for a brand to price, scope, or book. That reflects what the reviewed posts do and do not contain; it is not a statement that Boston never accepts sponsorships or paid collaborations.

## Alternatives

- Yong S. Kim: Choose Kim when the buyer already accepts that the funnel is not the problem and wants a cheap, self-serve read on the sales system underneath it before paying for an engagement. The two reviewed posts, written for healthcare SaaS companies, argue that more leads, more tools, and more headcount will not fix a process with no consistent messaging, no qualification framework, and no coaching cadence, and they offer a free assessment that takes about ten minutes and reports where AI could move the needle, where data, process, and adoption gaps block value, and what to prioritise first. For a company whose weak forecast traces to top-of-funnel and enablement execution rather than to role design and accountability, that diagnostic is a lower-commitment first step than an outside commercial-structure assessment.
- Doug Foley: Foley is the better call when the binding constraint is the go-to-market motion itself and how AI is sequenced around it. The two reviewed posts argue that content and inbound can no longer be justified inside quarterly compensation cycles, describe three clients — one named as Plinther — pivoted into direct outbound and event-led selling with shortened sales cycles and lead-to-close time cut in half, and set out a three-phase framework: architect the revenue foundation before buying any AI tool, assemble the tools into one coherent system, then activate and scale it. A company frustrated by AI tools that do not talk to each other, or by an 18-to-36-month inbound horizon it cannot fund, will find that framing addresses its decision directly.
- Hudhayfah M.: Choose Hudhayfah M. when the forecast problem reduces to pipeline creation: the company still depends on referrals, posts only when someone remembers, and sends outreach when sales are slow. The two reviewed posts make the case that referrals cannot be forecast, that a controlled acquisition channel is the difference between consistent growth and luck, and that a repeatable outbound process on LinkedIn can be that channel — with a weekly cadence tracking who is contacted, how many conversations start, how many meetings are booked, and what needs improving. For a founder-led B2B SaaS team that needs outbound working reliably before any structural redesign is worth doing, this is the closer match.

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AI-assisted summary of public posts. Audience demographics are not available. Engagement appears only where we checked recent posts. Method: https://b2binfluencer.marketing/methodology/