# Sean O'Shaughnessey

Sean O'Shaughnessey creates practical content about B2B sales and sales leadership. O'Shaughnessey co-hosts the Two Tall Guys Talking Sales Podcast and co-created the B2B Sales Lab, where salespeople and leaders discuss real sales challenges.

- Profile: https://b2binfluencer.marketing/creators/sean-oshaughnessey/
- LinkedIn: https://www.linkedin.com/in/soshaughnessey
- LinkedIn followers: 10,958
- Topics: artificial-intelligence, leadership, sales, ai-in-sales, sales-leadership, sales-forecasting, sales-coaching, outbound-sales, sales-compensation
- Based on 13 dated posts, latest 2026-09-22

## Summary

Useful for practical B2B sales and sales leadership content on forecast integrity, outbound systems, compensation, and AI.

- Best for: B2B sales enablement vendor co-marketing webinar on forecast integrity through disciplined discovery.
- Not for: Consumer or general-productivity brands wanting paid sponsorship with guaranteed impressions and verified demographics.
- Check first: Confirm co-marketing or paid partnership is acceptable and ask for audience and performance data.

### Takeaways

- Most forecast misses start in discovery, not at the close.
- Performance is a production system, not a call quota.
- Compensation plans, not salespeople, drive discounting and deal behavior.

## Main ideas

- **Most forecast misses start in discovery, not at the close**: O'Shaughnessey argues that forecast misses are often diagnosed as closing problems — a stalled deal, a champion gone quiet, new procurement requirements, a cheaper competitor — when the root cause was incomplete discovery months earlier. Weak discovery travels forward, contaminating stage progression, urgency assessment, and implementation assumptions. Pipeline volume can look healthy while forecast integrity quietly degrades. O'Shaughnessey puts the responsibility on management practice: leaders typically inspect deal momentum by asking whether the next step is scheduled, rather than whether the business case has been validated, the economic buyer is engaged, or implementation constraints have surfaced. Their fix is structural: stage definitions and forecast criteria should require documented discovery details before an opportunity reaches a commit-worthy stage.
- **Performance is a production system, not a call quota**: On outbound, O'Shaughnessey says the usual conversation starts with the wrong question: how many calls each salesperson should make. Consistent results depend on a complete operating system. Raising the call target without that infrastructure, they argue, produces more wasted activity rather than qualified pipeline. Their question for leaders: has the company built an outbound production system or simply handed salespeople a list and told them to call it?
- **Adding another tool does not fix a broken operating system**: O'Shaughnessey applies the same systems logic to sales technology. A rep can have a CRM, contact database, intent data, a sales engagement platform, conversation intelligence, LinkedIn, and enrichment tools, they note, and still spend the first two hours of the day talking to zero buyers. They call that an operating-system problem, not a technology shortage. On AI, their argument is that volume becomes cheap when AI can automate it, and therefore less valuable. The advantage shifts to deciding who deserves attention right now, why the timing matters, what is worth saying, which signal deserves action, and when a human should take over. O'Shaughnessey assigns monitoring, enrichment, prioritization, and repetitive execution to AI, while experienced sellers handle buying-committee politics, hesitation, unexpected questions, commercial judgment, and trust building.
- **Compensation plans, not salespeople, drive discounting and deal behavior**: Using an end-of-quarter deal, O'Shaughnessey shows how a plan that pays on revenue while nobody is measured on margin can reward giving away profit: the salesperson is rewarded for revenue, the manager needs the deal for the forecast, and the larger commission goes out on the smaller-margin contract. They frame that as a compensation-design problem rather than a salesperson problem. The central issue, they say, is not whether AI can calculate commissions faster, but whether leadership has clearly decided which behaviors deserve to be rewarded. They treat the tools under discussion as ways to model plan costs, simplify commission rules, improve transparency, and test incentives before rollout — not as substitutes for that decision.
- **Sellers should drive their own development, and a classroom course is not the answer**: O'Shaughnessey collects quota-attainment figures from several studies and concludes that many capable salespeople are missing their numbers. They separate factors outside a seller's control — territory, product-market fit, pricing, leadership, quota design, marketing support — from what a seller can control. A career, they argue, should not depend on whether an employer supplies coaching, judgment, and development. Their alternative to formal training is a place to bring specific deal questions as they arise, rather than a multi-day methodology course that is hard to apply in a live deal.
- **A durable practice built on a weekly show and a live audience**: The recurring formats are part of the argument, not just distribution. O'Shaughnessey co-hosts the Two Tall Guys Talking Sales Podcast with Kevin Lawson, which reached its 200th episode after nearly four years of weekly fifteen-minute conversations about sales and sales leadership, and produces episodes of AI Tools for Sales Pros that end in a practical framework. Across their posts, the structure is consistent: a reframe in the first line, a short diagnostic of what leaders get wrong, a numbered list of components or questions, and a closing route to the podcast episode or the B2B Sales Lab.

## Work to read

- [Discovery Quality Is a Forecast Integrity Issue](https://www.linkedin.com/posts/soshaughnessey_discovery-quality-is-a-forecast-integrity-activity-7508137055600672768-2FUj)
- [Cold Calling Is Not an Activity. It Is a Production System.](https://www.linkedin.com/posts/soshaughnessey_cold-calling-is-not-an-activity-it-is-a-activity-7484241823834566656-0TxD)
- [Your sales compensation plan may be undermining your sales strategy](https://www.linkedin.com/posts/soshaughnessey_artificialintelligence-aisales-salescompensation-activity-7490156068178653184-qfx0)
- [Your salespeople probably don't need another prospecting tool](https://www.linkedin.com/posts/soshaughnessey_your-salespeople-probably-dont-need-another-activity-7495455361513222144-vvhA)
- [Missing quota isn't unusual. That's precisely why you shouldn't accept it as inevitable.](https://www.linkedin.com/posts/soshaughnessey_missing-quota-isnt-unusual-thats-precisely-activity-7503436359798464512-DEaV)
- [200th episode of the Two Tall Guys Talking Sales Podcast](https://www.linkedin.com/posts/soshaughnessey_i-truly-feel-honored-we-just-recorded-our-activity-7494030122497372160-rZx4)
- [Preparing for the 200th episode and nearly four years of weekly sales conversations](https://www.linkedin.com/posts/soshaughnessey_i-cannot-believe-that-we-are-preparing-for-activity-7488605586343964672-m1bJ)

## Brand relationships

- **B2B Sales Lab** (disclosed_partnership)
- **Two Tall Guys Talking Sales Podcast** (mention)
- **AI Tools for Sales Pros** (mention)

## Partnerships

The posts do not describe a sponsorship, paid-placement, or brand-partnership format. They name no sponsor and provide no rate card, media kit, or booking route. The recurring commercial call to action is the B2B Sales Lab, a community Sean O'Shaughnessey co-created with Kevin Lawson and promotes as a place where salespeople and leaders bring real deal questions (b2b-sales-lab.com). That is their own venture, not a sponsorship slot for outside brands. Compensation platforms — Forma.ai, QuotaPath, Everstage, Pigment, and Salesforce Spiff — appear as the subject of an episode about plan design, not as announced partners. For a co-marketing webinar, ask directly whether they accept paid partnerships and confirm the deliverables and pricing; the posts provide neither.

## Alternatives

- Cory Bruscia: A better choice when the webinar should start one level up from discovery discipline: building the sales system a forecast can rest on. Bruscia's posts argue that hiring more salespeople will not fix a broken foundation and list what that foundation needs — a defined sales process, documented ICP, consistent messaging, prospecting strategy, qualification methodology, CRM discipline, KPIs, and an onboarding plan. They also argue that companies should redesign the seller's role around what AI can do rather than pile tools onto the existing job. If the enablement vendor wants a session for founders and early revenue leaders titled something like 'build the foundation before you add people or AI,' Bruscia's material speaks directly to that brief, while Sean O'Shaughnessey's stays focused on the narrower question of what evidence must exist before a deal reaches a commit-worthy stage.
- Bryan Higgins: A better choice when the campaign is about pipeline execution rather than forecast quality: how outbound runs at scale, how quickly replies happen, how follow-up and re-engagement are automated, and how a sales team keeps AI systems trained on its own process. Higgins's posts report AI-driven outbound results while away from the desk (touches, reply rate, opportunities, booked appointments) and argue that AI SDRs usually fail because companies automate chaos instead of training the system on an existing sales process, ICP, and qualification framework. For a demand-generation or sales-operations webinar co-hosted with an AI SDR vendor, that is closer to the buyer's question than a discovery-evidence checklist.
- Anthony T. Gilliam: A better choice when the session should challenge the pressure system around selling rather than improve one stage gate. Gilliam's posts frame modern selling as a survival game where quota and activity metrics dominate, ask whether the system actually creates conditions for customers to buy, and argue that leaders respond to skill gaps with denial and more activity when the real need is teaching difficult conversations, better questions, feedback, and ownership. If the buyer wants a leadership-development webinar on why quota pressure and forecast pressure backfire, these posts speak to it; O'Shaughnessey's posts supply operator-level mechanics instead.

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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/