Sam Jacobs

For GTM software, he says the goal is not to enrich data or warm up email; it is to help sellers get meetings with buyers.

He contrasts feature-heavy software menus with the buyer’s actual goal, then uses the iPhone as an analogy: Steve Jobs removed buttons instead of adding more.

• In another post, Jacobs imagines CRM shifting from a database people maintain to a system of action that coordinates follow-up.
• He says relationships, trust, judgment, and empathy will still matter.

The CRM argument pairs automation with a clear limit: automate administrative work, while treating human relationships and judgment as more important, not obsolete.

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His advice emphasizes financial fluency, forecasting, team leadership, and coordination across Sales, Marketing, and Customer Success.

The CRO School syllabus he describes includes P&L fluency, unit economics, financial modeling, building a management team, and working with the board. In a separate career checklist, he advises managers to learn how companies create value, read financial statements, build their own forecasting spreadsheets, and tell stories with data.

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A high salary or target compensation figure does not by itself protect an executive from a substantial change in responsibilities.

He recounts advising a friend signing as CRO at a $50 million software company.

• Jacobs says the original contract treated missing a quarterly target as “cause.”
• He describes narrowing that definition, adding protection for material changes in role scope, and extending severance from three to nine months.
• When the company later changed the role, his friend received a $225,000 lump sum.
• This is one account, not a prediction of typical results.

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His approach is to frame the case around the buyer’s concerns and make the reasoning concrete.

In a chapter for Mutiny’s Buyer Experience Guide, Jacobs says the CFO speaks a different language from other stakeholders.

• He describes using John McMahon’s framework from The Qualified Sales Leader to walk through a nine-part economic-buyer presentation, including a worked example.
• That framework is attributed to McMahon, not presented as Jacobs’s original.

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He expects commercial judgment, storytelling, charisma, and individuality to stand out as routine execution becomes easier to automate. In a separate cultural argument, he says people should not try to sound uniformly professional when technology can produce that same polish.

In a post discussing a paper by Will Manidis and Joe Roberts, Jacobs says great sellers could be worth far more in the age of AI and that enterprise sales is not among the functions he expects to disappear. Separately, he uses Jimmy V’s idea of a good day—think, laugh, cry—to argue that eccentricity may become more valuable as AI-generated work becomes more alike.

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The prediction that a bubble will pop belongs to Topline guest Geoffrey Moore; Jacobs presents the planning list as a response to that possibility.

For a possible 2027 correction, Jacobs recommends a weekly 13-week cash forecast for bootstrapped companies, a downside case with explicit triggers, pressure-testing renewals, proving ROI, and modeling longer sales cycles. He advises quarterly planning rather than relying only on an annual plan.

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Sam Jacobs opens with the distinction he says matters most: a VP of Sales is measured on hitting the number, while a CRO is measured on the business.

• The evidence is the alumni response he keeps hearing — "I finally have a system" — and the eight-week CRO School syllabus, which is unusually specific: building a world-class management team, P&L fluency and unit economics, forecasting and financial modeling, scaling inside sales, foundations of marketing leadership, foundations of customer success, storytelling with data, and working with the board.
• Every session is taught by a named sitting operator: Kiva Kolstein (President and CRO at AlphaSense), Andrea Kayal (CRO at Help Scout), and Rick Smolen (CRO at Shiphero).
• The post closes with the practical detail of the next cohort: eight weeks, Thursdays, 90 minutes.

For brands planning a campaign

If you are evaluating a pilot workshop on CRO readiness, this is the existing product to measure against — the topic list, the operator-as-instructor standard, and the delivery format are all stated here, so a proposal that repeats them adds nothing.

In 2023 a friend was about to sign as CRO of a $50M software business and asked for a 20-minute review of the offer.

• The money was fine; the structure was not.
• The definition of "cause" was broad enough that missing a quarterly revenue target counted as grounds for dismissal.
• Sam Jacobs rewrote it around the conventional standard — ethical, moral, or legal violations — added language making a material change in responsibility, scope, or geography a constructive termination that triggers severance, and extended severance from three months to nine.
• Nine months into the job the company split marketing and customer success out of the role; the clause fired and the friend received a $225,000 lump sum.
• The post ends by naming the course built on this work: three live sessions on valuing an offer, reading the equity, and negotiating the protections executives miss.

For brands planning a campaign

This is close to ready-made teaching material for a compensation negotiation module: a named clause, a specific intervention, and a documented outcome. Any pilot session on this topic would be expected to work at this level of detail rather than in generalities.

Written from the vantage point of someone who is 49 and looking back, the list addresses frontline sales, marketing, or customer success managers who want a VP or C-suite role within three to four years.

• The steps mix relationships and financial literacy: build one or two relationships a week outside your company rather than only during a job search; help peers who will later run organizations; learn how companies create enterprise value and what investors buy when they fund debt versus equity; read a P&L and understand the difference between cash and revenue; build your own forecasting spreadsheets; learn to tell stories with data; find mentors five to ten years ahead of you; and read 20-30 books a year, fiction and history included, to sharpen metaphorical thinking.
• The closing pitch is the GTM Leadership Accelerator, with the claim that 31% of past participants have historically been promoted within 12 months of graduating.

For brands planning a campaign

This is the clearest view of the funnel: broad, genuinely useful free guidance, with a paid program at the end and a headline outcome statistic attached. Treat the 31% figure as the program's own claim; nothing in the supplied evidence verifies it.

Sam Jacobs quotes Geoffrey Moore, author of Crossing the Chasm, from a Topline conversation — "There is zero chance that this bubble doesn't pop" — then answers with ten planning moves: plan quarterly rather than annually; keep a 13-week cash forecast if you are bootstrapped; lean into agentic automation for operational productivity; build a downside case with explicit triggers for what changes if revenue lands 20% below plan; build the revenue plan around existing customers and pressure-test renewal assumptions; prove the ROI you sell so it survives a spending freeze; concentrate on the segment where you have a clear advantage; keep fixed commitments low; model slower buying decisions and longer approval chains; and equip the team you already have, naming RevOps and the GTM Leadership Accelerator first. The public alignment is explicit: four Pavilion schools launched that week.

For brands planning a campaign

A strong anchor for a workshop session on planning under uncertainty, and the clearest example of the media-to-training funnel — the interview comes first, the course recommendation second, in the same post.

The post recalls meeting Mutiny's Jaleh Rezaei when she appeared on Topline, and later working with the company at Pavilion dinners.

• The teaching point is that the CFO "speaks a different language than the rest of your stakeholders in your deal," and that getting a budget approved requires learning it.
• Sam Jacobs wrote the chapter on the economic buyer presentation in Mutiny's Buyer Experience Guide, built on John McMahon's framework from The Qualified Sales Leader, and describes walking through the nine parts of that meeting with a full worked example.
• He flags that John McMahon is a Topline guest that same week.

For brands planning a campaign

A usable template for pilot materials: a named framework, a nine-part meeting structure, and a worked example. The guide is produced with a vendor, so confirm reuse terms before building course content on it.

The argument is that GTM software is built by porting old workflows onto AI instead of reasoning from what AI makes possible, and the result is feature bundles where every capability ends up on the left-hand navigation.

• The customer-level point is blunt: people don't want waterfall enrichment or email warm-up, they want meetings with buyers, and the tool is not the thing being bought.
• The analogy is Steve Jobs erasing buttons from the iPhone rather than adding them.
• The post points readers to a Sundays with Sam essay called "Tabula Rasa," described as carrying a childhood story about Stuart Little.

For brands planning a campaign

Not course material, but it shows a second audience — product and GTM founders — and a second channel, the newsletter, which is where the longer argument lives. A workshop proposal that ignores this channel is leaving the distribution path unexamined.

The claim is that CRM as a database humans are obliged to maintain is ending after 30 years, and that in an agentic world it should become a "system of action" — understanding every interaction, identifying opportunities before a salesperson does, coordinating follow-up.

• Sam Jacobs is explicit about what survives: relationships, trust, judgment, and empathy matter more, not less; it is the administrative layer built around them that is ripe for reinvention.
• The post says the team at Attio is asking some of the right architectural questions, and carries the hashtag #attiopartner.

For brands planning a campaign

Shows how a company-adjacent take can be framed as an architecture question rather than a product pitch. The hashtag indicates a partnership program; it is a disclosure about the post, not evidence of payment, and no engagement claim about the creator's commercial relationships should be drawn from it.

Sam Jacobs builds on a paper called "Commanding Heights" by Will Manidis and Joe Roberts to argue that great sellers will make ten times what anyone else does in the age of AI, and that this is the golden age of sales rather than the end of it.

• The reasoning: people who combine commercial acumen, charisma, storytelling, and eccentricity will be paid disproportionately; large bureaucracies will struggle to compete for them, which is part of why founders pursue dual-class share structures that let them pay operators at market value; and enterprise sales is among the few functions not replaced.
• He anchors the claim in a named paper rather than assertion.

For brands planning a campaign

The premise a workshop proposal can stand on — that revenue leadership skill is worth investing in — and evidence of the reading habit behind the teaching. A pilot designed around this thesis should cite the underlying paper rather than the post.

In a partner-tagged post, Sam Jacobs describes CRM moving from a human-maintained system of record to an agent-driven system of action.

• Sam Jacobs also writes that great sellers will make 10x anyone else in the age of AI, that enterprise sales is not one of the functions AI will replace, and that one person plus agents can do work that used to take 5, 10, or 20 people.
• Concrete examples include CRM data entry, waterfall enrichment, email warm-up, and cobbling together data sources, which Sam Jacobs says buyers do not want; they want meetings with buyers.

First-principles product argument supported by customer-desire examples.

The Attio post carries an #attiopartner tag; the posts do not state payment terms or a formal review relationship.

For brands planning a campaign

A brand selling GTM, CRM, or AI productivity software can use Sam Jacobs to frame an agentic future while keeping the human seller central. The campaign should connect AI capability to buyer meetings and operator judgment, not just feature consolidation.

Examples: Source 1 · Source 2 · Source 3 · Source 4

The CRO School syllabus Sam Jacobs promotes covers building a management team, financial literacy and P&L fluency, unit economics, forecasting and financial modeling, scaling inside sales, marketing and customer success foundations, storytelling with data, and working with the board. Sam Jacobs says alumni report finally having a system and walking into board meetings with confidence.

Course syllabus plus alumni-reported outcomes.

For brands planning a campaign

A pilot workshop on CRO readiness can use this syllabus as an outline: financial fluency, board communication, cross-functional GTM alignment, and management systems. A brand can sponsor or co-host the session and ask Sam Jacobs to bring operator examples.

Examples: Source 1 · Source 2 · Source 3

Sam Jacobs focused on deal structure rather than total comp, flagged an excessively broad definition of cause, rewrote it around ethical, moral, or legal violations, added constructive termination for material change in scope, and extended severance from 3 to 9 months.

• When the role later changed, the friend received a $225,000 lump sum.
• Sam Jacobs says this is the work taught in Pavilion's Executive Compensation & Negotiation course: valuing an offer, reading equity, and negotiating protections.

Anonymous case story with before-and-after contract clauses.

The $225,000 outcome comes from one anonymous case and is not presented as a guarantee for other executives.

For brands planning a campaign

This is a strong proof point for an executive negotiation workshop or content series. A campaign can ask for a session on cause definitions, constructive termination, severance, equity, and change-of-scope triggers, with a worked example.

Examples: Source 1 · Source 2 · Source 3

The list includes weekly external networking, helping peers, understanding enterprise value and finance, institutional investment mechanics, reading financial statements, servant leadership, sales methodologies and qualification, storytelling with data, using AI for business insights, building forecasting spreadsheets, auditing other departments' reports, mentoring relationships, reading 20-30 books a year including fiction and history, and cross-functional relationships. Sam Jacobs ties the list to Pavilion's GTM Leadership Accelerator and says 31% of participants have been promoted within 12 months.

Numbered self-assessment checklist.

The 31% promotion figure appears in course promotion material and is not independently verified in the supplied posts.

For brands planning a campaign

A brand targeting ambitious frontline GTM managers can use this as a detailed career-development hook. The pilot workshop can address this audience as well as current CROs, with practical finance, AI, and sales-funnel modules.

Examples: Source 1 · Source 2 · Source 3

Sam Jacobs recommends RevOps and GTM Leadership Accelerator for existing teams.

List distilled from a podcast conversation.

The advice is framed for a possible 2027 correction and draws on a podcast guest's prediction, not a guaranteed forecast.

For brands planning a campaign

Brands selling GTM, finance, or revenue operations tools can sponsor practical downturn-planning content. The campaign should emphasize cash, triggers, renewals, ROI proof, and segment focus rather than generic resilience.

Examples: Source 1 · Source 2 · Source 3

Sam Jacobs also stresses storytelling with data in leadership courses and the ability to tell stories with data as a career skill.

Cultural reference plus argument about AI and value creation.

This theme is opinion and commentary, with fewer data points than the operating posts.

For brands planning a campaign

For brand campaigns, Sam Jacobs can carry a human-differentiation message inside B2B revenue content. Pair this theme with concrete sales, leadership, or data-storytelling examples so it does not become abstract inspiration.

Examples: Source 1 · Source 2 · Source 3

The Mutiny Buyer Experience Guide chapter covers the economic buyer presentation, uses John McMahon's Qualified Sales Leader framework, and walks through the nine parts of the meeting with a full worked example. Named guests and operators include Jaleh Rezaei, Geoffrey Moore, John McMahon, and CRO School instructors such as Kiva Kolstein, Andrea Kayal, and Rick Smolen.

Recurring multi-format teaching model.

For brands planning a campaign

A brand can evaluate Sam Jacobs across more than one format: podcast guest, newsletter feature, live workshop, webinar, or guide chapter. A pilot workshop can be packaged with a worked example and named operator contributors.

Examples: Source 1 · Source 2 · Source 3 · Source 4 · Source 5

In the Mutiny guide chapter, Sam Jacobs says the CFO speaks a different language from other stakeholders and that budget approval depends on learning it. Other posts emphasize sales funnel construction, qualification, entry and exit criteria, and the claim that great sellers will be worth 10x others in the age of AI.

Practical sales framework and buyer-side presentation walkthrough.

For brands planning a campaign

For sales enablement, qualification, or revenue software, Sam Jacobs can connect product messaging to buyer-side decision mechanics and economic-buyer presentations. A campaign should use specific selling frameworks rather than follower-count claims.

Examples: Source 1 · Source 2 · Source 3 · Source 4

Sam Jacobs also points to Topline episodes, Sundays with Sam, webinars, and direct messages for enrollment. Posts often end with a DM invitation or a request to comment.

Recurring promotional pattern across posts.

For brands planning a campaign

The recurring programming creates repeatable placement options: course sponsorship, cohort integration, webinar, podcast episode, or newsletter feature. A brand should expect the content to include a course or community call to action alongside the editorial message.

Examples: Source 1 · Source 2 · Source 3 · Source 4 · Source 5 · Source 6

He writes that executive compensation negotiation is "the work I'll be teaching in Pavilion's Executive Compensation & Negotiation course," describes an eight-week CRO School syllabus as "our" syllabus, tells readers to DM him for a personal invitation, and announces upcoming CMO, Partnerships, RevOps, and GTM Leadership Accelerator cohorts. The posts show a teaching and promotional role; they do not spell out his title or the formal terms of his relationship with Pavilion.

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The post presents a working collaboration on the guide; it does not state payment or a sponsorship arrangement.

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The post does not describe payment, a contract, or any other specific commercial terms, so this is treated as commentary plus a stated partner tag, not as documented sponsorship.

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Knutzen also frames the choice between buying software and building with AI, a question Sam Jacobs raises when discussing CRM and GTM tools.

Knutzen writes as a hands-on practitioner sharing specific projects and tools: a reusable context document, a time-tracking dashboard, mileage automation, changed expectations for CRM data. Sam Jacobs writes at the leadership level, with course syllabi, compensation negotiation, board communication, and arguments about where the field is heading rather than a log of tools tried.

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Portnoy concentrates on partnerships and partner-led revenue, arguing that the function's real gap is data, benchmarking, and the metrics a CFO already trusts. Sam Jacobs ranges across CRM, buyer-side selling, CRO readiness, and executive compensation rather than advocating for one channel.

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The overlap is easiest to see for a reader who arrived through revenue operations rather than sales leadership.

Lent's two published posts are a revenue operations job posting and a recommendation of a colleague, not teaching or commentary, so the similarity sits in subject area and role vocabulary rather than in format or argument. Sam Jacobs's material is instructional and opinionated, with worked examples and frameworks.

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The two posts are practitioner accounts of exactly that.

• One reports finishing Pavilion's AI in GTM school, working through hands-on exercises alongside peers, and building 35 projects for personal and business use, listing a master context document that can be attached to any prompt, a marketing campaign setup, a website, automated mileage tracking, a time dashboard, and travel planning.
• The other reports themes from a session with SaaS CROs: preparation, follow-up and CRM hygiene standards are now unforgivable to miss, AI-assisted preparation is the minimum expectation, forecasts can be pressure-tested for risk and opportunity, automatic call scoring can coach account executives and managers, and vendors should be made to prove their tools interoperate with the buyer's data platform and go-to-market motion.
• A 90-minute workshop on how a revenue team actually uses AI week to week, from prep to forecast review to coaching off call data, can be built from these posts directly, with each participant producing one working artifact and sharing it back.

There is no material on offer terms, severance, equity, change of scope, or any other part of the executive compensation brief, and nothing on the CRO career path itself.

• Neither post shows a course, cohort, or coaching program that Nick Knutzen runs; one post describes attending someone else's school, so instructor credentials, curriculum, format, and fee would all have to be established from scratch.
• The posts are also short: the AI detail is a list of outputs, not teaching material, so a session built here needs new preparation time.
• If the buyer's actual problem is preparing people for the CRO seat and negotiating their contracts, switching to this person changes the subject of the pilot, not only the teacher.

Examples: Source 1 · Source 2

One post says they are returning to Pavilion's GTM Conference to present an agentic playbook for making partner revenue predictable, arguing that partner-led deals carry better unit economics through higher win rates, lower customer acquisition cost and better retention, and that most companies never build the channel seriously because no CFO will fund something that cannot be modeled.

• The other reports asking dozens of CEOs, CROs and CMOs at a conference what would make them invest more in partnerships, finding that most believe partnerships can work but hold back because they do not know what good looks like, and concluding that partnerships trails other go-to-market functions on ROI, framework, performance and benchmarking data.
• The practical ask in that post is specific: track win rate, sales cycle, average contract value and cost per dollar sourced.
• For a sponsor whose pilot is building a partner program or defending partnership spend to a finance lead, that is closer to the brief than CRO-readiness teaching.

Nothing in the two posts covers employment contracts, compensation, equity, or severance, so the negotiation half of the proposed pilot cannot be taught from this evidence.

• There is also no cohort course, syllabus, or coaching offer documented, only conference speaking and field interviews, so the delivery format and artifacts would have to be designed from zero.
• The subject shifts from a revenue leader's own readiness and contract to a go-to-market channel, which changes the audience and the sponsor's budget line.
• Neither post shows a rate, a booking route, or any comparable engagement result.

Examples: Source 1 · Source 2

One post is a job description for a Director of Revenue Operations at Blue Heron, a luxury homebuilder, reporting to the chief marketing officer and spanning alignment across Sales, Marketing and Client Experience, with scope covering process optimization, forecasting accuracy, pipeline analytics, enablement strategy and revenue technology stack performance.

• The other is a referral for a colleague moving from customer experience, customer success and product support into product work.
• If the buyer's real difficulty is that nobody owns revenue operations, or that sales, marketing and customer experience are pulling apart, these posts speak to that problem more directly than a course would.

Neither post shows teaching, a course, a cohort, or coaching, and neither touches compensation negotiation or CRO readiness, so almost none of the proposed pilot maps onto this material.

• The context is a vertically integrated design and construction firm selling ultra-luxury homes, not B2B software, and the range and pace of that sales motion differ from the sponsor's.
• Both posts are from 2025 with nothing later supplied.
• Choosing this route swaps a leadership-development workshop for a hiring or org-design conversation, which is a different purchase with a different budget owner and a slower path to a pilot.

Examples: Source 1 · Source 2