Two Tall Guys Talking Sales cover art

Two Tall Guys Talking Sales

Two Tall Guys Talking Sales

Written by: Kevin Lawson and Sean O'Shaughnessey
Listen for free

About this listen

 "Two Tall Guys Talking Sales," where Sean O'Shaughnessey and Kevin Lawson discuss a single sales topic. Kevin and Sean together have about 60 years of experience in professional selling. This podcast helps people in sales, sales leadership, and business leadership or company owners realize the maximum value of their company by improving their revenue generation capability. This podcast is designed to help those people enhance their companies' sales management practices, methodologies, processes, teams, and messaging. Sean O'Shaughnessey and Kevin Lawson are Fractional Vice Presidents of Sales. They operate their own companies separately but have partnered for this podcast to advise salespeople and SMB companies on successful strategies and methodologies. Kevin is the CEO of Lighthouse Sales Advisors. Lighthouse Sales Advisors is a sales leadership solution provider for small businesses. Lighthouse helps business owners navigate the potential pitfalls around sales growth, sales turnaround, or scaling up by leveraging sales acumen and decades of experience to build effective sales teams. https://www.lighthousesalesadvisors.com/ Sean is the CEO of New Sales Expert. He helps company owners realize the maximum value of their company by improving their revenue generation capability. He helps owners enhance their sales management, methodologies, processes, teams, and messaging.2024 Economics Management Management & Leadership
Episodes
  • Sales Territory Plan 2026: The Sales Management Blueprint for Revenue Generation

    Sales Territory Plan 2026: The Sales Management Blueprint for Revenue Generation
    Jan 20 2026
    If you're serious about sales success in 2026, this episode is a gut-check and a blueprint. Sean and Kevin break down what a real territory plan looks like (not a fluffy "be more productive" wish list), how to map first-half revenue to specific accounts, and how to build a second-half pipeline before it's an emergency. The throughline is sales management discipline: define the goal, allocate time intentionally, and build a plan that survives reality—because it will get punched in the face. Key Topics Discussed Why most reps are under-planned—and why that's unacceptable if you want Sales success (00:00) Sean frames the problem: Day-to-day selling without a plan is a strategy for mediocre revenue generation. Territory plan vs. account plan: what you should build first (01:00) Territory planning starts with "who will buy and how much," not activity lists or generic prospecting promises. First-half revenue mapping: list your closeable accounts and expected revenue (02:00) If your sales processes assume a sub-6-month cycle, you should already know which deals can land in the first half. Second-half pipeline sourcing: identify 3–10 prospect channels, not names (02:31) Kevin ties it to repeatable sales strategies: pipeline creation is a system, not a mood. Strategic vs. key accounts: time allocation, long-cycle wins, and reputation as an asset (04:00) Kevin introduces a time-based framework: strategic "marriage-level" accounts vs. key near-term wins, and the reputational groundwork that makes both easier. Pricing, comp alignment, and the real math of revenue management (07:42) If you're "opening a territory," your pricing plan and comp plan have to match the reality of getting noticed versus optimizing margin. Key Quotes Sean: "If you fail to plan, then you plan to fail." (00:00) A blunt reminder that planning is not optional if you want predictable revenue generation. Kevin: "At the top of the sheet, write your goal." (04:00) Start with the outcome, then design your territory plan around time and focus—not random activity. Sean: "Your plan for 2026 has to equal or exceed your quota." (10:39) Your plan should be a commitment to performance, not a narrative that explains shortfalls in advance. Sean: "Everybody has a plan until you get punched in the face." (14:00) Build for volatility—plan to 120% so you can still hit quota when reality disrupts your assumptions. Additional Resources MEDDPICCC / qualification frameworks referenced as examples of structured sales processes you should use (09:00) B2B Sales Lab mentioned as a place to get your territory plan reviewed and "beaten up" by experienced sales leaders (14:38) A Significant Actionable Item from this Podcast Write a one-page territory plan today with four elements: (1) your 2026 goal (quota and your 120% number), (2) the list of accounts you expect to close in the first half with revenue per account, (3) 3–10 specific prospecting channels you'll use to source second-half opportunities, and (4) the five companies you will learn so deeply—business model, competitors, how they make/lose money—that your messaging and value selling approach becomes inevitable, not improvised. Summary Most reps treat territory planning like paperwork. Sean and Kevin treat it like a weapon. If you want sales success that's driven by business acumen—not hope—this episode gives you a practical territory plan structure, a way to allocate time across strategic and key accounts, and a reality-based view of revenue management, pricing, and comp alignment. Listen to it early in the year, build your plan, and you'll start running your territory instead of reacting to it. B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/ You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/ You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/
    Show More Show Less
    18 mins
  • From 0% to First Deal: January Sales Strategies to Start Strong

    From 0% to First Deal: January Sales Strategies to Start Strong
    Jan 13 2026

    It's January, the scoreboard is still 0 to 0 for most sellers, and the difference between a clean Q1 and a scramble often comes down to one thing: getting to "zero to one" without doing something stupid to win a deal you'll regret. In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O'Shaughnessey use a basketball fast-start analogy to sharpen your Sales strategies for early momentum, tighter Sales processes, and better Revenue management—without defaulting to discounting, panic, or hope-as-a-plan.

    Key Topics Discussed

    • Why the first "bucket" matters in Q1 (and how fast starts change the game) (00:00–02:15)

    • Zero to one: picking the highest-probability path to get on the board (02:15–05:30)

    • Buyer readiness: the "fast food vs. interstate exit" test for prioritizing your pipeline (03:00–05:10)

    • Reverify everything: deals inside 45 days, shifting priorities, and MEDDPIC discipline (06:45–10:20)

    • Don't get squirrely: protecting Value selling and profitability when you're tempted to "do something crazy" (10:35–13:10)

    • Sean's practical tax tip: mileage documentation that saves pain later (13:25–14:20)

    Key Quotes

    • Sean: "It's time to score that first bucket. It's time to go." (02:01)

    • Kevin: "You have to discern as a seller… who is the most likely to buy now." (03:35)

    • Sean: "Every deal that's on your forecast for the next 45 days, you need to touch base." (08:45)

    • Kevin: "Pause. Think about the deal you want… you're conditioning somebody how to buy from you." (10:54–11:20)

    • Sean: "Take a picture of your odometer… you'll thank me a year from now." (13:35)

    Additional Resources

    • MEDDPICCC qualification concepts referenced in the conversation (Champion vs. Coach; reconnecting with the Economic Buyer as the calendar turns).

    • Mileage-tracking best practice: capture odometer readings now to support business mileage documentation at tax time.

    A Significant Actionable Item from this Podcast

    Pick up the phone today and re-verify every deal on your forecast that's expected to close in the next 45 days (and don't accept vague answers). Confirm priorities didn't shift post-holidays, validate your Champion and Coach are still in seat and aligned, and re-confirm the Economic Buyer's expectations and paperwork path. That single discipline move is sales management in action, and it's how you protect Revenue generation without resorting to margin-killing "quick wins."

    Summary

    If you're sitting at 0% of quota in mid-January, this episode is your gut-check and your playbook. Sean and Kevin cut through the noise with practical Business acumen: prioritize buyers who are ready now, tighten your Messaging around value instead of price, and pressure-test your forecast so Sales success doesn't depend on luck. Listen if you want a fast start that holds up all year—because January habits become full-year outcomes.
    Show More Show Less
    17 mins
  • Start From Zero: January Sales Mindset, Pipeline Hygiene, and Q1 Revenue Generation

    Start From Zero: January Sales Mindset, Pipeline Hygiene, and Q1 Revenue Generation
    Jan 6 2026

    January resets every scoreboard to zero, making your mindset and operating discipline your first competitive advantage. In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O'Shaughnessey break down how to start the year with intentional sales management, tighter Sales processes, and the kind of daily actions that drive Sales success and consistent Revenue generation, especially when Q4 either "drained the swamp" or left you with deals that slipped.

    Key Topics Discussed

    • Why January mindset matters more than motivation (and how to avoid "being behind" by month-end) (00:00)

    • CRM data hygiene as a revenue lever: clean stages, real close dates, clear next steps (04:20)

    • Pipeline focus: prioritizing what you can actually work on, and aligning probability to reality (06:35)

    • Post-Q4 momentum: thank-you outreach that creates new expansion opportunities (08:05)

    • Prospecting with structure: start with five companies this week, then build the cadence (09:35)

    • Networking for leverage: partnering with adjacent vendors to unlock access and influence (10:40)

    Key Quotes

    • Kevin Lawson (04:55): "Stop. Go to your CRM and practice good data hygiene."

    • Kevin Lawson (05:55): "If someone has to ask you the status of your deal…your notes aren't good enough, your data hygiene isn't good enough."

    • Sean O'Shaughnessey (02:35): "Q1 started. You have quotas, you have a quota right now, and you have revenue of zero."

    • Sean O'Shaughnessey (08:10): "Go back and say thank you to every single one of your customers…and one of them is gonna say, 'but we need a little bit more.'"

    Additional Resources

    • B2B Sales Lab community (14:35): Join to get feedback, practical coaching, and peer support from sales pros, leaders, and marketers.

    A Significant Actionable Item from this Podcast

    Do a 30-minute pipeline reset today. Update your CRM with accurate stages, real close dates, and a clear next step for every active opportunity, then choose five target accounts to contact this week with a message tied to a specific business problem you solve. This single block sharpens your Messaging, improves Revenue management, and forces the Business acumen choices that separate busywork from real Value selling.

    Summary

    If you want a stronger Q1, this episode offers a clean operating model: tighten your Sales strategies and processes early, treat data hygiene as a performance habit, and build momentum through customer outreach, a structured prospecting approach, and intelligent networking. Kevin and Sean keep it practical, direct, and immediately usable, precisely what you need when January starts from zero, and Sales success depends on what you do next.

    B2B Sales Lab is a private, member-led community for sales professionals who want actionable insights, not theory. It's a space to ask real questions, share proven practices, and connect with others who are serious about improving revenue performance. Designed and led by veteran sales leaders, the Lab is where strategy meets execution. Join us at b2b-sales-lab.com

    You can reach out to Sean at New Sales Expert, LLC - Sean@NewSales.Expert - https://www.linkedin.com/in/soshaughnessey/

    You can reach out to Kevin at Lighthouse Sales Advisors & Sales Xceleration - kevin@lighthousesalesadvisors.com - https://www.linkedin.com/in/kwlawson/

    You can book time on Kevin's calendar at https://lighthousesalesadvisors.pipedrive.com/scheduler/JP7rZXH3/virtual-meeting-booking-time-with-kevin

    You can book time on Sean's calendar at http://newsales.expert/sean-oshaughnessey-calendar/
    Show More Show Less
    18 mins
No reviews yet