The Transaction

It’s painfully pitiful what passes as personalized prospecting presently. However, we’ve got just the guest to help sales reps get back on the right track.

Sam McKenna is the Founder of SamSales Consulting and is the foremost expert on social selling and leveraging LinkedIn to drive revenue. Sam and her team are redefining the go-to-market status quo for modern organizations through unmatched sales training and LinkedIn branding. Sam joins co-hosts Craig Rosenberg and Matt Amundson for a very fun and fascinating dive into how to improve your personalized sales messages to prospects, the secrets to successful social selling, and the best time to prospect. Plus, we share stories from some of our worst webinar fails. 

Also, Craig denies claims that he was in fact the heavy breather while hosting a webinar with Guy Kawasaki a decade ago and Matt reveals the truth about the size of a certain actor’s mouth.

Critical Takeaways

• Sales reps, please take 3 seconds to THINK before sending another stinky, smelly, no-good, automated email to a prospect. If you want to stand out to them and get their attention, earn it by doing the work that none of the other reps reaching out to them won’t. Show them you know them.
• A simple way to stand out to decision makers at target accounts is to engage with their LinkedIn posts. However, hitting “like” does not qualify as engaging in a way that will stand out. The smart play is to comment something insightful.
• Prospecting during non-working hours, like weekends and evenings, can capture the attention of busy executives. Emails sent during these times can stand out because prospects are usually less overwhelmed and more likely to engage with content beyond their regular work distractions.
• Don’t buy a ‘great new tool’ until you know what you’re going to do with it. Figure out how to solve the problem you’re addressing before you ever get close to buying a tech solution.

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Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Intro Sales Insights with Sam McKenna

04:38 Introducing Sam McKenna, Founder of SamSales Consulting

08:02 Announcing The New Sam McKenna Award For The Best Guest

10:13 A Particularly Titillating LinkedIn Controversy

11:44 The Airing of Our Webinar Woes

22:41 Companies Suck at Solving Problems & Try to Techstack Their Way Out of Issues

28:50 How to Run the “Been Awhile” B2B Prospecting Play using LinkedIn Sales Navigator

30:24 How to Use Social Selling in SaaS

34:40 Spearfishing for B2B Leads Using This Tactic on LinkedIn Sales Navigator

41:44 Why Putting in the Work is the Way to Wow Prospects and Customers

45:50 Why the "Show Me You Know Me" Method Works so Well for B2B Sales Reps

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Epic Quotes

• “ Why is it that so few people will just put in the actual work that that converts?” - Sam McKenna
• “ Anything that you can't automate won't be done.” - Matt Amundson

Connect with Sam

• LinkedIn: https://www.linkedin.com/in/samsalesli/ 
• Website: https://www.samsalesconsulting.com/ 
• Sam’s new Podcast: https://www.samsalesconsulting.com/showmeyoukknowmeshow/ 

Shoutouts

• Hayley Hoad: https://www.linkedin.com/in/hayley-hoad-2565549/ 
• Bobby Axelrod (Billions)
• Jill Rowley: https://www.linkedin.com/in/jillrowley/ 
• Paige Tills: https://www.linkedin.com/in/paige-tills/ 
• Joy Wilder Lybeer: https://www.linkedin.com/in/joywilderlybeer/ 
• Gail Moody-Byrd: https://www.linkedin.com/in/gailmoodybyrd/ 
• Adam Robinson: https://www.linkedin.com/in/retentionadam/ 
• Adam’s episode of The Transaction: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal 
• Toby Carrington: https://www.linkedin.com/in/tobycarrington/ 
• DocuSign
• ON24 
• Marketo
• Engagio
• Guy Kawasaki: https://www.linkedin.com/in/guykawasaki/ 
• Jon Gray: https://www.linkedin.com/in/jon-d-gray/ 
• DailyMail Article about the “LinkedIn Boobs Post”: https://www.dailymail.co.uk/news/article-14406563/linkedin-post-fury-comparing-woman-breast-size-confidence.html 
• Bobby Axelrod/Damian Lewis Tiny Mouth Investigation: https://www.maxim.com/entertainment/damian-lewis-tiny-mouth-2016-3/ 
• Reddit discussion of Bobby Axelrod/Damian Lewis’s tiny mouth: https://www.reddit.com/r/Billions/comments/8jcnx5/anyone_else_getting_annoyed_by_damian_lewis_tiny/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

You’ll be hard pressed to find a more energetic and experienced sales expert than our special guest, Maria Boulden!

Maria Boulden has spent over 3 decades creating and leading world-class sales teams at leading enterprise organizations like DuPont and Gartner. She brings her incredible experience in multiple verticals and truly unstoppable energy to one of the best conversations yet with co-hosts Matt Amundson and Craig Rosenberg. Maria drops some serious insight bombs in this one, including why steak dinners aren’t the deal closer that they once were, why top execs need to get down to the frontlines to talk with employees, and why ‘not broken’ is not good enough for your company to succeed. 

Additionally, there is some great advice in here about effectively leading change management efforts in your organization, why building personal relationships in SaaS has become so important for B2B sellers, and why you shouldn’t hold a deal signing at a Japanese gentleman’s club. Fueled by an ungodly amount of Coke Zero, Maria really brought it this episode and delivered some incredible stories, which make this a must-watch!

Also, Craig tests out a new hat and Matt admits he can be bought with a burrito. 

Critical Takeaways

• Senior leaders need to be visibly and vocally present with front-line sellers periodically. This not only boosts team morale but also ensures the leader understands the day-to-day challenges and can directly impart strategic guidance.
• Sales teams should focus on providing value and building genuine connections rather than relying on traditional wining and dining strategies.
• Waiting for 'normalcy' to return so you go back to old tactics is not viable. Leaders must guide their teams to adapt to the current market conditions and be prepared for continuous change.
• Conducting “pre-mortem” sessions can be an effective way to anticipate potential failures and mitigate risks before executing significant strategic changes. This approach can foster an environment of proactive problem-solving and better preparedness among the team.
• Helping clients understand their own business better and providing insights creates stronger, more trusting client relationships.

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The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Intro

00:44 Craig’s Special Hat

02:35 Introducing Maria Boulden

10:39 The Challenge with Channel Partners

19:31 Brazenly Baring It All

23:03 A Quick Conversation Regarding Caffeine

23:43 Steak Dinners have Gone Stale in Sales

33:42 Stories from the Signing Party & Where NOT to Hold One

36:48 Taking a Hands-on Approach to Leadership in Sales

38:17 Unbatten the Hatches & Adapting to Market Changes

41:56 How Executives Should Engage with Their Sales Teams

50:59 Delving into some Delicious Additions to Business Dictionaries

55:30 Wrapping Up

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Epic Quotes

• “ It was not my aspiration that they would have world-class sales skills, it was my expectation.” - Maria Boulden
• “ Not broken is not good enough in this environment.” - Maria Boulden

New Terms

• Donut Run (v): When a rep brings a box of joe and a box of donuts to meet with their distributor and ‘shoot the breeze’ for an hour.
• Ask Hole (n): Someone who continuously asks the same question, but never does anything with the suggestions they receive.
• Pre-Mortem (n): A proactive meeting held before executing a decision, campaign, etc., where the risks are clearly laid out along with what indicators should be monitored to determine real-time progress and what actions need to be taken mid-course.

Connect with Maria

• LinkedIn: https://www.linkedin.com/in/maria-boulden-8a778b11/ 
• Website: https://www.jsjrehoboth.com/ 

Shoutouts

• Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ 
• Dan’s Post: https://www.linkedin.com/posts/danielpgottlieb_good-luck-with-that-ai-theres-no-ai-on-activity-7293698734540955648-rNIz 
• Dan’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z 
• Nick Toman: https://www.linkedin.com/in/nicktoman/ 
• Nick’s Episode: https://thetransaction.substack.com/p/the-commercial-efficiency-crisis?r=3iae7z 
• Neil Rackham
• Spin Selling: https://a.co/d/1FSFtS1 
• Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ 
• Kyle Porter: https://www.linkedin.com/in/kyleporter/ 
• Kyle’s Episode: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers?r=3iae7z 
• Brent Adamson: https://www.linkedin.com/in/brentadamson 
• Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z 
• Ted Purcell: https://www.linkedin.com/in/tedpurcell/ 
• Bill McDermott: https://www.linkedin.com/in/billrmcdermott/ 
• Gartner
• DuPont
• Salesforce

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Michael King is one of the leading marketing executive recruiters working today and is also the author of a new book, Be There When I Return, a memoir of epilepsy, love, and success. Michael joins co-hosts Craig Rosenberg and Matt Amundson to discuss his personal journey with both epilepsy and his career, along with crucial career advice for marketing leaders looking for their next roles. Michael shares how the CEO should factor into your job search, why you shouldn’t chase titles, and the state of the job market for B2B marketing executives.

Also, Craig tries out a new look and Matt relives an epic beach party in Vegas.

Critical Takeaways

• Ensure the people you hire have relevant experience at companies similar in size and stage to your own. Avoid hiring someone just because they’ve been part of a larger company’s success unless their role aligns directly with what your company needs now.
• Chase companies over titles. Titles shouldn't be the defining factor when considering new positions. Joining a strong, growing company should be the priority as it offers career growth opportunities in the long run. Focus on the company's potential rather than the initial title, as the ultimate career growth lies in sustainable company success.

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The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Intro

02:58 Introducing Michael King

04:15 Michael's New Book & Incredible Personal Journey

09:29 Recruiting Career & Success Stories

18:54 Amazing Event Marketing Anecdotes

27:44 Falling in Love with a Brand

28:33 The Importance of Relevant Experience

33:55 Chasing Titles vs. Chasing Companies

39:14 The Value of Good Companies

49:03 Epilepsy Awareness and Personal Stories

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ If you go to a good company, you will never look for a job again.” - Michael King
• “ For success in your career, you chase companies, you do not chase titles; you do not chase money, you chase companies” - Michael King

Connect with Michael

• LinkedIn: https://www.linkedin.com/in/michaelking/ 
• Website: https://kingrecruiting.net/ 
• Book Website: https://www.michaeltking.com/ 
• Book signing in San Francisco: https://www.bookpassage.com/event/michael-king-be-there-when-i-return-ferry-building-store 

Shoutouts

• George Wallace
• Maria Pergolino
• Will Smith & DJ Jazzy Jeff Reunion at Everstring’s Pool Party: https://youtu.be/v6-QoeusjEs?si=2CynMyahkkqG1mT8 
• Jessica Cross
• Stephanie 
• Stacey Epstein
• David Mylam 
• Dave Arnold
• Michael Lundgren
• Miles Kelly
• Rob Bernstein
• Udi Ledergor
• Russell Udy
• SuccessFactors
• Salesforce
• Broadvision
• Okta
• Coupa
• Siebel
• Gong
• Cresta

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Employee churn is a serious problem that is seldom discussed, especially given how much of a detrimental impact it has on even the best companies. 

To help illuminate this problem and how to fix it at your organization, Katherine Andruha joins co-hosts Craig Rosenberg and Matt Amundson for a much-needed conversation filled with tips, tricks, and a few flamingos.

Katherine Andruha is the Vice President of Business Development at Fivetran and has led top-performing sales teams for decades at cutting-edge SaaS companies such as Simpplr, Cloudflare, Coursera, Eightfold.ai, Anaplan, Apttus, and Aruba Networks.

Katherine sheds light on where current onboarding programs fall short and shares what can be done so that employees are actually put in the best position to succeed. Additionally, Katherine dives into the importance of properly managing pipeline progression.

Also, Craig recounts getting “flocked”, Matt compliments Craig’s athletic abilities, and Sam the Producer grossly mispronounces someone’s name. 

Critical Takeaways

• A comprehensive onboarding process for BDRs is critical. Make sure new BDRs aren’t making live calls until week four. This allows them to become fully comfortable with the systems, processes, and their pitches, minimizing the risk of errors and increasing their initial successes.
• Utilize AI tools for mock calls to simulate real-world environments. This allows BDRs to practice handling objections and refine their pitches in a risk-free environment before they contact actual leads.
•  Incorporate various channels such as live calls, LinkedIn voice notes, and personalized videos. Ensure that new BDRs are trained to use these channels effectively as people are now more responsive to phone calls and LinkedIn interactions.
• Ensure that managers have a consistent checklist for onboarding and supporting BDRs. This will help maintain consistency and high standards across teams.
• Regularly review pipeline stages to ensure there are no stale leads. Utilize automated reminders for deals that have been stagnant for too long to push progression actively.

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Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Intro

06:30 Introducing Katherine Andruha

11:23 Onboarding and Training Challenges

19:25 Effective Onboarding Practices for B2B SaaS Companies

29:05 The Importance of Confidence in BDRs

30:37 The Sales Manager's Role in Onboarding

33:26 Territory Ownership and AE Handover

35:15 Creating a Fun and Productive Environment as a B2B Seller

37:45 Pipeline Progression and Accountability

42:48 The Role of CMOs in Pipeline Progression

44:57 Closed Lost Analysis and Product Feedback

48:01 The Importance of Phone Calls

48:41 Using Swag to Engage Prospects

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “Know your business. It's the only way you will be taken seriously.” - Katherine Andruha
• “Just call the leads” - Katherine Andruha

Connect with Katherine Andruha

• LinkedIn: https://www.linkedin.com/in/katherineandruha/ 
• Website: https://www.fivetran.com/ 

Shoutouts

• Doug Landis: https://www.linkedin.com/in/douglandis/ 
• Sangram Vajre: https://www.linkedin.com/in/sangramvajre/ 
• Alan Berkson: https://www.linkedin.com/in/alanberkson/ 
• Nooks: https://www.nooks.ai/ 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

There are more people than ever involved in deals on both the vendor side and customer side, and it’s having a massively negative impact on B2B growth.

Nick Toman is the Chief Product and Transformation Officer at SBI (Sales Benchmark Index) and is the third and final co-author of The Challenger Sale we’ve had on the show. Nick brings some amazing new sales and business research to dive into with co-hosts Matt Amundson and Craig Rosenberg. Nick unveils the effect that having more sellers involved has on win rates, the three behaviors of B2B salespeople that lead to the best commercial relationships, and why actions that seem like they would slow down deals are actually the key to closing them faster. Matt sparks an interesting discussion around sales compensation and the impact it has on both the behaviors of B2B sellers and the growth of the company on the whole. Toward the end, Nick teases his new concept of 'Headway Selling,' which focuses on actually helping customers reach their goals rather than simply selling them as much useless crap as possible.

Also, Craig recounts his childhood trauma of growing up a Dodgers fan in San Fransisco, Matt practices to be a court stenographer, and Sam the Producer confesses to an affinity for gnomes (?).

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Critical Takeaways

• Not only have buying groups grown immensely, but the number of people working on deals with those buying groups has also exploded. There are now an average of 12 people in buying groups and 5 people involved with the sale from the vendor side. This has led to a spike in confusion for buyers and a sharp decline in win rates for salespeople.
• The role of CSMs (Customer Success Managers) has devolved to have an extremely broad remit that is too big for them to actually deliver on effectively. In an ideal world, the CSM role should be to use very clear signals to identify customers who are struggling with adoption or retention issues and help them solve those issues. As it stands, many CSMs provide ongoing services and end up competing with account managers to land expansion and renewal opportunities. The competition on its own is one thing, but once the business is compensating both the CSM and the AM, there’s an issue with cost and efficiency.
• B2B sales reps need to focus on deeply understanding and aligning with customer initiatives. Sellers should be thinking about how they can help customers grow in their own businesses and avoid roadblocks. Gaining this deeper understanding of customer needs drastically shortens sales cycles and increases deal sizes.
• There are 4 main archetypes of behavior for people in commercial roles: 1. Narrowing- Closing early, Closing often. 2. Provoking - Provocative insights to redirect customer thinking (AKA: Challenger). 3. Translating - Detail & data-oriented to help customers understand impact. 4. Anticipating - Help customers think through the process and future challenges. 
• Of those 4 archetypes, the two that perform best in sales are Translating and Anticipating. The research showed that sellers exhibiting those behaviors actually closed deals more quickly and for more money than sellers using the Narrowing or Provoking behaviors. 

Sponsored Segment

Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Coming Up in this Episode...

00:40 Will the Real Nick Toman Please Stand Up

01:53 Introducing Nick Toman, Co-Author of The Challenger Sale

03:09 The Impact of The Challenger Sale in B2B Sales

13:55 Commercial Efficiency is Crippling B2B SaaS Growth

21:22 Is Sales Commision Getting out of hand for B2B Companies?

28:22 Why Don't Buyers Want to Talk to Sellers Anymore?

31:05 Key Behaviors for Successful Commercial Relationships

33:53 Why Starting Fast Is So Critical for Sales Success All Year Long

36:27 Strategies for Effective Sales Execution to Start the Fiscal Year Strong

41:08 Understanding The Four Commercial Role Archetypes & Their Impact on Deal Velocity

48:54 Customer-Centric Selling and Trust Building

53:56 Headway Selling & Delivering Real Customer Success

Epic Quotes

• “ You’ve got to help the customer make headway and you don't want to make headwinds.” - Nick Toman
• “ Commercial efficiency- the yield on dollars spent in sales and marketing- has gone down 50 plus percent.” - Nick Toman
• “ Those who really do situate themselves in a path of helping the customer evolve their business and get things right do much better than those who are like ‘Buy this thing.’” - Nick Toman

Connect with Nick Toman

• LinkedIn: https://www.linkedin.com/in/nicktoman/ 
• SBI Website: https://sbigrowth.com/ 
• Latest Research - How a Fast Start to the Year Defines Your Growth Outcomes: https://sbigrowth.com/tools-and-solutions/how_a_fast_start_defines_your_growth_outcomes 

Shoutouts

• Matt Dixon: https://thetransaction.substack.com/p/decoding-sales-indecision-with-matt?r=3iae7z 
• Brent Adamson: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z 
• The End of Solution Sales - HBR Article: https://hbr.org/2012/07/the-end-of-solution-sales 
• Dave Brock: https://thetransaction.substack.com/p/really-knowing-your-customer-with?r=3iae7z 
• Mike Bosworth: https://www.linkedin.com/in/mikebosworth/ 
• Neil Rackham
• Harvard Business Review: https://hbr.org/ 
• Karen Freeman: https://www.linkedin.com/in/karenefreeman/ 
• Stop Trying to Delight Your Customers - HBR Article: https://hbr.org/2010/07/stop-trying-to-delight-your-customers 
• AJ Gandhi: https://thetransaction.substack.com/p/navigating-market-success-with-aj?r=3iae7z 
• Vantage: https://www.vantage.sh/ 
• Ben Schaechter: https://www.linkedin.com/in/bensign/ 
• Marlin Equity Partners: https://www.marlinequity.com/ 
• Gartne...

There’s a lot of confusion about how to find the champion of your product within a buying group.

To help sort things out for B2B sellers, we invited Krysten Conner on the show! Krysten is an extraordinary sales coach who is hired by top SaaS revenue organizations to train their sales teams into incredible teams. Krysten has also made a number of courses available for purchase through her website and through pclub.io. Krysten joins co-hosts Matt Amundson and Craig Rosenberg to break down three ways to identify and develop strong champions within the buying group to help you close more deals. Krysten also shares the secrets to mastering multi-threading for sellers and how to maintain deal momentum with prospects so they become customers.

Also, Craig shares the playbook he used to land his first girlfriend, Matt adds an “s” where he shouldn’t have, and Sam the Producer puts his foot squarely into his big mouth.

Critical Takeaways

• There are three ways to proactively discover a champion within a prospect's buying group: 1. Do they do work asynchronous of your meeting with them? 2. Do they bring other people to follow-up meetings? 3. Do they have a point of view on the next steps?
• The first person to reach out or take a meeting with a seller is not necessarily the champion within that organization for your product or service. Don’t make the mistake of assuming they are the champion. Talking with you makes them a contact, not a champion, by default.
• “Typically” is a magic word to use in your sales calls. Buyers are very risk-averse and want to be sure they’re not doing something wrong that will get them fired. By sharing what other buyers “typically” do when it comes to things like next steps, you can give buyers peace of mind. 
• Buyers aren’t experts at buying your product, so you need to teach them and guide them to make the right decision. This process of educating buyers and helping them avoid common pitfalls makes them feel much more comfortable.

Sponsored Segment

Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 - Intro

03:44 - The "Let Me Help You Get this Car" Story

07:24 - Krysten’s Embarrassing Sales Stories

13:22 - Develop a Champion, Don’t Wait For Them to Show Themselves

18:39 - Examples of Asynchronous Work that Champions will Do

25:58 - Champions will Bring More People to Follow Up Sales Calls

32:36 - Craig Details how he Landed his First Girlfriend

33:35 - Who Should be Doing Asynchronous Work Within The Buying Committee

41:54 - Does Your Buyer have a Point of View on the Next Steps

44:54 - Mass Email Does Not Count as Multi-Threading

51:10 - Who a Champion Is and What They Will Do in The Buying Cycle

Sign up for our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “ You multi-thread, by single threading.” - Krysten Conner
• “ When I'm sending actually any email, if it's no one's baby, it's an orphan.” - Krysten Conner

Connect with Krysten Conner

• LinkedIn: https://www.linkedin.com/in/krystenconner/ 
• Website: https://krystenconner.com/ 
• Access the Free Slides Krysten Shared in this Episode: https://docs.google.com/presentation/d/1DOf9bsPh0m7WtQxwhlJfT7Yg22LkD3iukivIk0W1cOA/edit?usp=sharing 

Shoutouts

• Chris Orlob: https://www.linkedin.com/in/chrisorlob/ 
• Chris Orlob's Episode of The Transaction:
• Krysten’s Multi-Threading Course with pclub: https://go.pclub.io/multi-threading-masterclass 
• Mark Kosoglow: https://www.linkedin.com/in/mkosoglow/
• Mark Kosoglow's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false
• Scott Barker: https://www.linkedin.com/in/ssbarker/
• Scott Barker's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/selling-like-a-real-human-being-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 

Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Without a real point of view, your company, your product, and all of your amazing features will drift into irrelevance amidst the soothing currents of the sea of sameness we see in the state of SaaS. (Just learned about this thing called alliteration!)

To help you avoid that terrible fate and aid you in developing your positioning, we are thrilled that Bob Wright, the Founder of Firebrick Consulting, joined co-hosts Craig Rosenberg and Matt Amundson on the show. As a B2B Marketing expert, Bob has helped hundreds of B2B companies define and refine their positioning over the last several decades and is one of the foremost authorities on the subject working today.

In this episode, Bob illuminates the criticality of ‘selling the problem, not the solution’, why B2B positioning should be a CEO-led initiative, and the three questions that your positioning must answer for buyers.

Also, Craig eats the world’s loudest piece of chocolate and Matt tries to hire another guest while live on the podcast.

Critical Takeaways

• Sell the Problem, Not the Product. Focus on identifying and articulating the key problem your product solves for the customer. This creates urgency and relevance in the buyer's mind, making them more likely to engage with your solution.
• Your positioning should answer three key questions: 1. Why now? 2. How are you different? 3. Why does it matter to the customer? These answers create a compelling narrative that drives customer interest and action.
• Stop focusing on the features. Emphasize the broader business impact and outcomes in your B2B marketing, rather than detailed product features. This approach resonates better with executive buyers who are more concerned with strategic advantages.
• Shift from explaining how your product works, to inspiring the customer on why it matters to them. This makes your marketing message more compelling and memorable, driving stronger customer engagement and commitment.

Sponsored Segment

The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Highlights

01:56 Introducing Bob Wright, the Founder of Firebrick Consulting

07:36 Differentiate your B2B Brand or Die

17:22 Portfolio Positioning Challenges

22:00 Targeting the Right Buyers with your B2B Marketing

23:55 Expanding into New Markets

28:56 Maintaining Focus While Growing

31:06 The Importance of CEO Involvement

33:34 Effective Business Positioning Strategies

37:15 AI’s Impact on Positioning

41:52 Measuring Positioning Success for Your B2B company

42:48 Analyst Influence and Market Trends

44:51 Explaining Positioning to the Board

47:11 The Role of Storytelling in Positioning and B2B Marketing

Join our Newsletter: https://thetransaction.substack.com/

Epic Quotes

• “Sell the problem, not the product.” - Bob Wright
• “Don't waste all your go to market investments on shitty messaging.” - Bob Wright

Connect with Bob

• LinkedIn: https://www.linkedin.com/in/findurtruegenius/ 
• Website: https://firebrickconsulting.com/ 

Shoutouts

• AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ 
• Okta
• Microsoft
• Oracle
• SAP
• HPE
• Gartner

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Selling B2B has always been hard. The crazy buying frenzy of the ZIRP era was the exception, not the rule, so if you’re expecting the current buying climate to change any time soon, you need to readjust your perspective.

Scott Barker, Partner & Co-founder of GTMfund and Host of The GTM Podcast, joins Host Craig Rosenberg and special guest-host Scott Albro to talk all things sales, venture capital, and go-to-market. Scott (Barker) shares why focus can give sales reps superpowers, the outsized impact of warm introductions when building pipeline, and how focusing on uniquely human skills can help you excel in sales. There’s also some great discussion around the importance of accountability and ownership throughout your go-to-market team.

Also, Craig pitches both Scotts on launching a legal practice, Scott Albro relives the glory days of selling TOPO services, and Sam the Producer attempts to crack the case and catch the Bottle Cap Culprit.

Critical Takeaways

• Invest time in becoming an expert in the problems you are solving for your customers. Offer valuable insights that make clients see you as invaluable.
• Focus on the human side of sales, including trust-building and relationship management; that’s what closes deals. Rely less on pure automation or technology and more on human connections.
• Sellers can emulate what works in founder-led sales by using personal testimonies about why they joined the company or how the product solved a problem for them. This can make their pitch more relatable and compelling.
• Warm introductions are the best way to build pipeline in what is quickly becoming an AI-dominated selling landscape

Sponsored Segment

The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 Intro

00:26 Retreading Brent Adamson’s Maggots on a Plane Story

02:30 Introducing Scott Barker

05:10 Funny Fundraising Stories

08:33 The Importance of Humanizing Sales

12:59 Overcomplicating Pipeline Generation

16:25 The Human Side of Sales

19:39 How to Build Trust in Sales

22:08 Expertise in Sales: Lessons from TOPO

29:46 The Concept of “Opinionated Software”

34:39 Overcomplicating Pipeline Generation

38:19 The Power of Warm Introductions

43:36 Scaling Founder-Led Sales

52:59 The Value of Human Skills in the Age of AI

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Epic Quotes

• “ If you even have the thought of an excuse as a sales leader, as a seller, as a marketer, you're already dead in my books. It requires full and complete accountability.” - Scott Barker
• “ If there are things that are stopping you from doing your job, it is nobody else's problem, but your own” - Scott Barker

Connect with Scott Barker

• LinkedIn: https://www.linkedin.com/in/ssbarker/ 
• GTMfund Website: https://www.gtmfund.com/ 
• GTMfund’s new fundraising announcement: https://techcrunch.com/2025/02/04/how-max-altschuler-accidentally-founded-a-vc-firm-that-just-raised-another-54m/ 
• GTMnow Website: https://gtmnow.com/ 
• The GTM Podcast: https://gtmnow.com/tag/podcast/ 

Shoutouts

• Brent Adamson: https://www.linkedin.com/in/brentadamson/ 
• Brent Adamson’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false 
• Max Altschuler: https://www.linkedin.com/in/maxaltschuler/ 
•  Javier Soltero: https://www.linkedin.com/in/jsoltero/ 
• Zendesk
• Anthropic
• Microsoft
• Google
• Neil Harrington: https://www.linkedin.com/in/neildharrington/ 
• Jim Cyb: https://www.linkedin.com/in/jimcyb/ 
• Vinny Pazienza, AKA Vinny Paz and Vinny “The Pazmanian Devil" Pazienza
• Bleed For This (2016, Ben Younger)

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When your buyer isn’t confident in the decision they’re making, they will choose not to decide. Meaning, that you’re not going to close that deal, which is a serious problem in B2B.

To help solve that problem, we’re thrilled to welcome Brent Adamson, the co-author of The Challenger Sale and renowned sales speaker, to the show. Brent joins hosts Matt Amundson and Craig Rosenberg to discuss the crucial sales topics in his new upcoming book, The Framemaking Sale. They get into the problem with value-selling, why sellers need to teach buyers how to buy with confidence, and where thought leadership is falling short in today’s environment.

Also, Craig pitches an idea for a radical new podcast and Matt cuts to the front of the line to call dibs.

Critical Takeaways

• Focus more on building customer confidence in their own decision-making abilities rather than just showcasing the value of your product. If customers are reluctant or unsure, they will likely delay or avoid purchasing altogether.
• Bring implementation and customer success representatives into pre-sale discussions. This helps reassure the customer that post-sale support will be robust and demonstrates your commitment to their success.
• Instead of just showcasing customer success stories, position them as a tool to show customers how to buy so that new customers understand the buying process and pitfalls to avoid. This gives prospects practical advice and increases their confidence in making a complex decision.
• Optimize your sales process to lose deals quickly. If a deal is likely to be lost, aim to lose early rather than late. This saves your sales team time, resources, and focus for more promising opportunities.

Sponsored Segment

Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 - Trailer

01:25 - Introducing Brent Adamson

03:51 - I’m Tired of these MFing Maggots on this MFing Plane

10:08 - The Impact of Buyers’ Low Confidence in Themselves

18:42 - Buyers Don’t Know How to Buy

23:44 - Implementing a Objectives, Tactics, Results Approach to Sales

30:49 - The Problem with Replicating Successful Sellers

36:26 - Thought Leadership & Content Marketing’s Role in Building Confidence

40:49 - How to Building Customer Confidence

45:16 - The Role of Founders in Sales

51:39 - Wrap Up

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Epic Quotes

• “Solve for customer’s confidence in themselves” - Brent Adamson
• “ It's not that I'm selling badly, it's that customers are buying badly.” - Brent Adamson

Connect with

• LinkedIn: https://www.linkedin.com/in/brentadamson 
• Website: https://www.brentadamson.net/ 
• A to B Insights Website: https://atobinsight.com/
• Maggots on a Plane Video: https://youtu.be/BFp30CkVcLo?si=aDSKIeQOTfyt9IZ5 

Shoutouts

• Karl Schmidt: https://www.linkedin.com/in/karl-schmidt-q/ 
• Bryan Smith: https://www.linkedin.com/in/bryankeithsmith/ 
• Tyler Harnish: https://www.linkedin.com/in/tylerharnish/ 
• Marc Benioff: https://www.linkedin.com/in/marcbenioff/ 
• Sense-making for Sales in HBR: https://hbr.org/2022/01/sensemaking-for-sales  
• Matt Dixon: https://www.linkedin.com/in/matthewxdixon/ 
• Stephen Powell: https://www.linkedin.com/in/stephen-powell-06996785/ 
• Kevin Hendrick: https://www.linkedin.com/in/kevinhendrick/ 

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When you can tell your story in a compelling, confident way, you can change the lens through which everyone views you, your accomplishments, and your potential.

Dia Bondi, a TEDx speaker, author of Ask Like An Auctioneer, and executive coach, joins Hosts Craig Rosenberg and Matt Amundson for an exceedingly energetic and entertaining conversation focused on communicating effectively as a leader. In between some fun tangents, they dig into how to uncover and craft your origin story to tell a more compelling narrative, why doing live demos on stage needs to go the way of the dodo, and how to raise more funding without a pitch deck. They also discuss their favorite examples of leaders who are actually doing this well and showing the world who they really are. Strap in for a fun and informative fifty-two minutes that every aspiring leader needs to hear (or watch if you’re on Spotify or YouTube).

Also, Matt mixes up 1960s movie characters named Felix and Craig channels his inner Sully as he desperately attempts to land multiple planes.

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Critical Takeaways

• When someone asks you who you are, don’t rifle through the bullets of your resume. Instead, tell them the narrative of your origin story. Include the core things that drive you, the context around why you set out to do X, and who you really are.
• Speaking on stage is too expensive for you to have a live demo of your product that doesn’t work. It’s much better to have a pre-recorded demo for your presentation and then give people an opportunity to interact with a live demo at your booth where things are lower stakes if the product fails.
• Founders need to realize when to hand off the tactical duties in their all-hands meetings, such as being the emcee or running a slide deck. Your team needs you to show up at the status that matches the role that people need you to play in the world.
• All-hands meetings are extremely expensive, especially the ones that are run poorly and time-intensive. You need to allocate your team’s time carefully based on what is most important to the company’s mission, so make sure not to squander that precious time.
• Being a compelling communicator is not about being perfectly polished, it’s about staying true to yourself and adapting your natural approach to each context while maintaining authenticity.

Sponsored Segment

The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/

Interested in becoming a sponsor of The Transaction? Contact [email protected]

Chapters

00:00 - Intro

00:20 - Craig comes Straight Outta Compton

00:58 - Fun Facts about Dia Bondi, Matt, & Softball

04:09 - Introducing Dia Bondi

08:20 - The Impact of Establishing Your Voice

12:13 - What is Founder Unrest & When Does It Show Up?

15:19 - How Founders can Find Their Own Voice & Unlock Their Origin Story

20:42 - Why Understanding How to Tell Your Origin Story Matters

31:12 - Dump the Live Demos from your Presentations

33:15 - Wait, How Expensive are All-Hands Meetings?

38:20 - Two Big Misconceptions about Communication

43:44 -  Examples of Leaders with Great Perspectives & Well-Developed Voices

50:04 - Craig Compliments Sam for Displaying Basic Competence

50:24 - Wrapping Up

Epic Quotes

• “ Founders are always going into conversations that are bigger than their britches. That's kind of like a job requirement.” - Dia Bondi
• “ To win and to differentiate today, we need the founder to reach trusted superstar status as fast as possible.” - Craig Rosenberg
• “ I think of founder voice as something you lend to your venture.” - Dia Bondi

Connect with Dia

• LinkedIn: https://www.linkedin.com/in/dia-bondi/ 
• Website: https://www.diabondi.com/ 
• Dia’s TED Talk: https://youtu.be/mFtHKTgyjyU?si=oElL9kWENAiSMary 
• Ask Like An Auctioneer (Book): https://www.asklikeanauctioneer.com/ 
• Dia’s Resource Library: https://www.diabondi.com/resources 

New Terms: 

• Buttwing (v): To guesstimate. See Also: Ballpark

Shoutouts

• Claire Sua-Amundson: https://uclabruins.com/news/2013/4/17/208207255 
• Claire Pitching to Dan Le Batard: https://youtu.be/o-HM5Sm5omA?si=3yzu1TtT_tD5mUyq 
• Funny Article about Claire and Matt: https://vault.si.com/vault/2005/06/06/-hitting-the-big-time 
• Dan Le Batard: https://lebatardaf.com/ 
• The Odd Couple (1970-1975)
• Howard Schultz: https://www.linkedin.com/in/howardschultz/ 
• Howard Schultz Interview on Acquired: https://youtu.be/A0fvX-wV70Y?si=-Ljn1jqTYP5aGEaR 
• Starbucks: https://www.starbucks.com/   
• Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ 
• Jensen Huang Interview on Acquired: https://youtu.be/y6NfxiemvHg?si=bfv8w-1wgTZk5l6A 
• Nvidia: https://www.nvidia.com/en-us/ 
• Nick Mehta: https://www.linkedin.com/in/nickmehta/ 
• David Solomon: https://www.linkedin.com/in/david-m-solomon/ 

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