Josh Roth shares practical advice on sales leadership and go-to-market teams, including forecasting, sales compensation, moving upmarket, and using AI in sales workflows.
Josh Roth offers practical B2B sales leadership and go-to-market advice for brands reaching sales and revenue leaders.
A B2B sales-technology company reaching sales and revenue leaders about improving sales execution.
A consumer lifestyle brand seeking broad-reach entertainment with no B2B sales connection.
Check first: Confirm interest, terms, required disclosures, and audience composition before planning a paid collaboration.
Josh Roth shares practical commentary on B2B sales leadership and go-to-market work.
Josh Roth connects sales-management advice to the decisions and behaviors behind it.
Josh Roth offers practical, results-oriented advice on optimizing B2B sales and GTM operations, with a focus on aligning revenue functions, choosing strategic markets, integrating AI, and maintaining leadership presence to drive high deal value and retention.
Roth argues that compensation plans often fail when operations teams design them without input from the sales staff responsible for executing the strategy.
The disconnect between rewards and field realities drives top performers to leave.
Roth says siloed policies can create chaos: when an initial compensation plan is reintroduced four months later, A-players leave.
Roth advises sales organizations to raise average deal size by targeting selectively and enforcing strict deal qualification rules, shifting the focus from volume to value.
At one company, the strategy was to cut all deals under $5,000 and focus on the top 31% of accounts, eventually increasing the average deal size from $3,108 to over $42K.
Roth cautions that sales leadership is not a path away from selling; it is a crucial force multiplier.
Leaders who become too absorbed in internal processes risk losing touch with market signals.
Roth says that when sales leaders step away from customer calls, they start managing CRM hygiene and relying on internal dashboards instead of understanding what customers are telling them.
Roth says that true competitive advantage requires transforming the entire go-to-market technology stack to be 'AI-forward,' not merely adding AI tools to an existing software-heavy workflow.
Roth highlights tools such as AI engagement scores, which can help gauge stakeholder interest and direct sales effort toward the most relevant opportunities and people.
Sales forecast calls should not collect optimistic or pessimistic status updates.
Their purpose is to establish the objective truth about a deal's current state, risks, and actual likelihood of closing.
Roth critiques common forecast call participants, such as 'Happy Ears Harry' who overpromises, or 'Red Cell Ryan' who lacks substantive deal movement, emphasizing the need to filter out wishful thinking.
For companies with high sales-team turnover, this article explains how organizational silos undermine retention and how to address the underlying policy issues.
Josh Roth explains that compensation plans designed by Operations without meaningful input from Sales often drive extreme turnover among top performers (A-players), because the plans miss field realities and revenue drivers.
Brands targeting CROs or HR leaders in B2B SaaS can use this to frame collaborative go-to-market strategies as essential to team stability and retention, and position their services as a solution to organizational misalignment.
This post offers sales leaders a step-by-step playbook for moving away from small, unprofitable deals and increasing average deal size.
Roth outlines a systematic approach: qualify out small deals (< $5K), adopt structured sales methodologies (Force Management, Joint Success Plans), shift focus to the top 31% of revenue-driving accounts, and concentrate efforts in specific industry niches.
Consulting firms and sales enablement software providers can use this to show how their services help companies sharpen go-to-market focus and improve average contract value.
This piece frames AI adoption in sales as a strategic leadership challenge, not simply a software decision.
Roth argues that to stay competitive and retain A-players in the AI era, sales teams must fundamentally transform their sales and revenue operations tech stacks to be AI-forward, rather than simply adding generative AI to existing workflows.
Vendors selling advanced AI/CRM integrations can use this to shift the conversation from “use ChatGPT” to “systemic transformation of business processes” and reach C-level decision-makers.
For sales leaders concerned about customer relationships, this post challenges the idea that leadership means stepping away from selling.
Roth critiques the trend of sales leaders withdrawing from customer interactions and relying on reports and CRM hygiene. They argue leaders should stay actively involved in deals to gather market signals, improve coaching, and maintain genuine customer insight.
Sales management training programs and leadership coaches can use this to highlight the value of “deep field” experience for executive decision-makers.
This practical, humorous guide helps sales managers make forecasting meetings productive, honest, and decisive.
Roth takes on familiar stereotypes of forecast-call participants—the overly pessimistic, the overly optimistic, the distracted, and the passive—to argue that the meeting’s real purpose is to rigorously extract deal reality from the pipeline.
Sales methodology trainers and CRM implementation partners can use this to show how they help streamline sales processes and improve forecasting accuracy.
Josh Roth critiques compensation plans dictated by operations without crucial input from sales.
Misalignment often ignores field realities and drives turnover among top sales performers (A-players).
Brands can apply Josh Roth’s insights to improve sales structure by building compensation plans collaboratively with revenue-generating teams, rather than imposing them top-down through internal functions.
Examples: Source 1
Roth argues that sales leadership is not an escape from selling but a force-multiplier function.
Leaders who avoid daily customer interaction risk losing touch with market signals and relying on CRM data that may not reflect customer truth.
Organizations refining their RevOps leadership models can use Roth's observations to create protocols that keep executives engaged in the customer lifecycle and deals.
Examples: Source 1
Roth provides a framework for substantially increasing average deal size by cutting low-potential accounts and focusing on the highest-value segments.
This involves strict deal qualification rules and structured sales methodologies.
Define criteria for high-potential accounts (e.g., industry focus, revenue potential) and implement deal flow filters (e.g., minimum deal size, required meetings) to streamline the pipeline.
Brands targeting Enterprise or specialized mid-market sales cycles can use Roth's advice to build playbooks focused on high-growth industries and accounts, putting sales teams where the money is.
Examples: Source 1
Roth offers guidance on running high-stakes forecast calls by identifying and calling out dysfunctional reporting, including excessive optimism, outright pessimism, and a lack of substantive deal progress.
Set clear expectations for forecast calls, prioritizing objective deal status and risk assessment over high-level performance rhetoric.
Sales management and operations leaders seeking more accurate, honest revenue projections can use Roth's framework to uncover the truth of a deal rather than accept surface-level optimism.
Examples: Source 1
Roth advocates moving beyond basic AI use in sales and transforming the entire tech stack to be AI-forward, using tools like AI Engagement Scores to prioritize efforts and support high-performing salespeople.
Integrate AI-driven workflows and engagement scoring into GTM motions to inform resource allocation and deal prioritization dynamically.
For B2B SaaS companies, these insights can guide technology investment in sales, showing how to use AI not just for productivity but to optimize commercial strategy and give A-players a competitive advantage.
Examples: Source 1
Josh Roth’s posts promote hiring at Gorgias and feature trumpet’s AI Engagement Score.
Ask whether they work at Gorgias and what relationship they have with trumpet.
Mention
Roth’s posts direct readers to sales openings at Gorgias and mention its San Francisco office.
Disclosed partnership
In a post about AI in sales, Roth presents trumpet’s AI Engagement Score as a way to assess stakeholder engagement and prioritize deal work.
Josh Roth examines the operating choices that help B2B sales teams produce more predictable revenue: compensation-plan design, customer engagement by leaders, deal-size growth and forecast scrutiny.
Start with the compensation post for a concrete failure story, then read the deal-size post for a step-by-step turnaround, the field-leadership post for a management argument and the forecasting post for a practical way to question pipeline claims. The AI post is the most commercial and tool-specific; read it after the operating posts to see how they frame technology as a leadership and process issue, not a standalone tactic.
Both treat revenue operations as the function that makes forecasts less surprising.
They examine the gap between a clean-looking plan and what the sales floor can deliver, linking operating detail to leadership consequences.
Aleman focuses on board communication, hiring-plan capacity math and behavioral risk signals in the CRM. Roth ranges across compensation design, deal-size discipline, field leadership and AI in the sales stack.
Both focus on whether pipeline and forecast claims hold up to scrutiny.
They ask readers to test deal progress against evidence rather than accept stage labels or optimistic reporting.
Hines builds a single diagnostic question into a worked client example with before-and-after numbers. Roth uses recognizable sales archetypes, compensation failures and leadership habits to make the same point.
Both write about compensation-plan design as cross-functional revenue operations work with direct behavioral consequences.
They examine who owns the plan, what data should inform it and how it changes salespeople’s behavior.
Milligan centers the ownership question and RevOps career positioning. Roth focuses on compensation failure modes, deal-size growth, field leadership and hiring.
Josh Roth’s LinkedIn content offers practical, strategic advice for sales and revenue operations leaders.
They address operational challenges in modern B2B SaaS growth, including optimizing sales compensation to improve GTM team alignment, using AI to enhance sales efficiency, and refining deal structures to target higher-value, upmarket accounts. Their discussions are geared toward executives and managers responsible for scaling and optimizing sales and revenue functions.
Josh Roth's LinkedIn posts focus on sales methodology, Go-To-Market (GTM) strategy, and internal operational excellence in the SaaS sector.
Ask them about formal partnership programs, sponsorship policies, specifications, and inquiry routes for external collaborations; these are not disclosed.
Good fit: a B2B sales-technology company wants to reach sales and revenue leaders with a campaign about improving sales execution. Josh Roth’s posts give the campaign a concrete editorial foundation: they argue that sales leaders should stay involved in customer deals, describe focusing teams on larger, better-qualified accounts, and say AI should be built into broader sales workflows rather than treated as a cold-email shortcut. These angles suit a product that can demonstrate a specific improvement to sales work. The campaign should teach or show a useful practice, not imply that Josh has endorsed a product or achieved results with it. Before planning a paid collaboration, confirm interest, terms, and any required disclosures.
Poor fit: a consumer lifestyle brand wants a broad-reach entertainment campaign with no connection to B2B sales. The posts center on sales leadership, revenue operations, forecasting, compensation, and AI in go-to-market workflows. The humor—for example, the invented forecast-call characters in the forecasting post—supports the explanation of a sales problem rather than establishing a general entertainment format. A buyer should not assume that an unrelated consumer message will feel natural or reach the brand’s target audience. Ask for audience-composition data before deciding whether Josh’s LinkedIn followers match a particular consumer segment.
Hypothetical brief: A B2B sales software company wants to help revenue leaders improve forecast-call quality. Decision: A plausible content fit, subject to confirming that Josh is open to a partnership. Campaign angle: “Four forecast-call habits that hide deal risk—and questions leaders can ask instead.” A post could use the four contrasting characters from Josh’s forecast-call example as a memorable opening, then give readers a short checklist for testing what is real, what is stalled, and what is wishful thinking in a deal. Introduce the sponsor only where its product demonstrably helps with that task, and substantiate claims against product information. This angle follows Josh’s emphasis on extracting deal truth rather than accepting optimism or pessimism at face value. Before commissioning, agree on the format and approval process, verify product claims, and request audience data relevant to sales and revenue leaders.
Choose Jose Aleman when the campaign’s central task is making a sales capacity plan or forecast hold up in practice.
The posts cover the arithmetic of hiring reps against quota, ramp time, pipeline supply, manager span, and territory damage, and argue for reading buyer behavior rather than rep-entered sentiment. That’s a sharper match than Josh Roth’s broader mix if the sponsor sells capacity planning, forecast inspection, or revenue-operations cadence.
The reviewed work focuses on planning and forecast mechanics, with less direct material on compensation-plan design or AI-enabled sales workflows—topics Josh Roth covers more directly. For a broader go-to-market or compensation narrative, ask for additional examples.
Choose Jennifer Hines when the campaign needs to connect AI investment with sales execution discipline and pipeline qualification.
The posts contrast how leadership communicates AI spending and lay out a milestone-based way to test whether pipeline is real. This is a strong fit for a sponsor selling sales training, qualification, or revenue-process improvement tied to an AI story.
The posts focus more on diagnosis and communication than on compensation mechanics or upmarket deal-size strategy.
Choose Ryan Milligan when the campaign centers on who owns compensation-plan design and how revenue operations can coordinate finance, sales leadership, and reps to test changes.
The post directly addresses this cross-functional problem, including reviewing commissions against plan and asking whether reps behave as intended. This suits a sponsor with a compensation-planning or revenue-operations product.
The posts offer limited coverage of AI-enabled sales workflows and upmarket deal execution.
Examples: Source 1
Editable Markdown templates for planning a campaign with this creator.
