The Transaction

Most B2B brands (yes, probably yours) think that they’re ‘customer-centric’, and yet none of them ever stop droning on and on about their product and its ‘revolutionary’ features.Lauren Goldstein is the Chief Growth Officer of Winning by Design and Co-Founder, Board Member, Chair of the Board of Directors for Women in Revenue. Lauren joins co-hosts Craig Rosenberg and Matt Amundson to chat how B2B sellers and marketers can connect with buyers in the way buyers want them to, why having a diverse leadership team is an invaluable asset for any startup, and why “Strategic RevOps” is enabling breakthrough growth for SaaS startups.Also, Craig shocks the world by caping for his portfolio companies’ sales pitches, and Matt mentions the production design aesthetic of a niche director.Critical TakeawaysImplement structured mentorship programs in your org where experienced team members can guide less experienced colleagues, as this can lead to increased job satisfaction and retention, on top of the personal and professional development of your whole team.Instead of spending time on a sales call waxing poetic about the ‘revolutionary’ features of your product, use that time to ask your prospect what success looks like for them. How are they measured as a success or failure? Uncover that ideal state and help them understand how your product can get them there, provided it actually can; otherwise, don’t waste their time and yours.Consider using ‘Reverse Demos’, where instead of showing off your product right away, you have the customer outline their current processes and challenges. While this approach might not work with all types of buyers, it could be effective in understanding complex systems and better tailoring your pitch to the customer's actual needs.Cross-functional alignment across your go-to-market team is crucial. Sales, marketing, product, and finance teams need to work collaboratively, understanding each other’s objectives and challenges. Regular inter-department meetings to align goals and strategies help everyone move in the same direction towards shared business goals.Companies that have strategic RevOps roles are better at aligning their sales and marketing efforts with financial and operational goals, ultimately driving growth and operational efficiency.Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview00:30 - Are the Angels a Real Team & Breaking Down the Backgrounds03:24 - Introducing Lauren Goldstein, Chief Growth Officer of Winning By Design & Co-Founder of Women in Revenue06:36 - The Origin Story of Women in Revenue (The group, not the concept)18:17 - The Immutable Impact Diverse Teams in Business23:43 - B2B Tech Brands Are NOT Connecting Buyers in the Ways That SaaS Buyers Want31:39 - What is a ‘Reverse Demo’ & Why is Gartner Analyst Dan Gottlieb Recommending it36:00 - Revenue Growth in SaaS Comes Back to Identifying the Right Buyers40:43 - The Critical Role of Rev Ops in B2B Go-to-Market Strategy for SaaS44:00 - Strategic Rev Ops: The Key to Integration & Go-To-Market AlignmentSign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“ Managing multiple stakeholders in an enterprise sale is not a new thing. But it's more than managing multiple stakeholders, it's really about helping to facilitate a conversation where they're all understanding the problem in the same way and can connect back to a common denominator.” - Lauren Goldstein“ There is no greater liar as a buyer, than a marketer.” - Matt Amundson (A Marketer)Connect with LaurenLinkedIn: https://www.linkedin.com/in/laurengoldstein/ Winning by Design Website: https://winningbydesign.com/ Women in Revenue Website: https://womeninrevenue.org/ ShoutoutsSydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with Katharine Reagan: https://www.linkedin.com/in/katharine-reagan/ Shari Johnston: https://www.linkedin.com/in/sharijohnston/ Jen Dimas: https://www.linkedin.com/in/jenpd/ Tracy Eiler: https://www.linkedin.com/in/tracyeiler/ Jim Walker: https://www.linkedin.com/in/jwwalker/ Robert Koehler: https://www.linkedin.com/in/rkoehler/ RadiusMarketoMaria Pergolino: https://www.linkedin.com/in/mariapergolino/ InsideViewBabcock JenkinsDan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Episode: ​​https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb MiroMark Kosoglow: https://www.linkedin.com/in/mkosoglow/ Mark’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity Kelly DeHart: https://www.linkedin.com/in/kelly-dehart-18b63315/ Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Colin Gerber: https://www.linkedin.com/in/colinsgerber/ SocureAdam B. Needles: https://www.linkedin.com/in/abneedles/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/the-new-go-to-market-blueprint-with AnnuitasLove the show? Give us a shoutout on LinkedIn and tell us what you loved!

Ana Leyva advises early-stage startups at Pear VC on their go-to-market strategy to help them build stunning sales motions that set them up to scale. Ana provides pre-seed and seed startups with her first-hand experience as a seasoned operator with past roles at tech unicorns Box, ServiceTitan, and Vanta. Ana joins Co-Hosts Craig Rosenberg and Matt Amundson to delve into how to transition beyond a founder-led sales motion without losing their special perspective, why insight-driven outreach beats crappy sales personalization in B2B, and the two foundational pillars that you need to have in place to build a strong go-to-market strategy.Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company.Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter.Critical TakeawaysThe crappy bit of personalization you grabbed from LinkedIn and added to your stale cold outbound email is not going to set you apart. ‘We went to the same school’ doesn’t help that decision maker develop a solution to the problems they’re facing.Rather than relying on bare-minimum ‘personalization’, put your thinking cap on and reach out with a business insight that can actually help your prospect learn more about their business, understand their problem better, or make a more informed decision.As hard as it can seem to turn down customers early on, founders need the discipline to focus on prospects who will truly benefit from their product, and saying no to the wrong fit is crucial for building long-term customer relationships.The bedrock of your go to market strategy should be built upon endless customer obsession and very strict ICP (Ideal Customer Profile) parameters. That ensures you deeply understand the pain your customer solves and can build a product to solve that pain effectively. Don’t just let your customers come to you, you need to pick the right protagonists for the epic narrative that you are creating for yourself and your customers. Be picky about who you allow to join and steer the arc of this grand story you are embarking on. Sponsored SegmentInterested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.comChapters00:00 - Episode Preview00:20 - Squishy Pineapples & The 1995 UCLA Bruins04:01 - Introducing Ana Leyva, GTM Leader at Pear VC08:29 Selling at B2B Conferences on the Road as a New Mom 11:32 - Focus on Providing Value, not on Bland “Personalization”21:33 - B2B SaaS Founders Need to Rewrite New Go To Market Playbooks27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup45:06 - Is Cold-Calling Coming back in Style for SaaS Sales Teams?Sign up for our Newsletter: https://thetransaction.substack.com/Epic Quotes“I am sick of personalized emails.” - Ana Leyva“I always tell our founders, you’re not selling for the initial close; you’re selling for the renewal.” - Ana LeyvaConnect with AnaLinkedIn: https://www.linkedin.com/in/analeyva/ Pear VC Website: https://pear.vc/ ShoutoutsAJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ Brandon Redlinger: https://www.linkedin.com/in/brandonredlinger/ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’s Episode: Jen Allen-Knuth: https://www.linkedin.com/in/demandjen1/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Jason’s Post on LinkedIn: https://www.linkedin.com/posts/jasonmlemkin_so-theres-a-lot-of-angst-on-linkedin-about-activity-7308223252420509697-EJCSStevie Case: https://www.linkedin.com/in/steviecase/ Scott Albro: https://www.linkedin.com/in/scottalbro/ GongScott Barker: https://www.linkedin.com/in/ssbarker/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!

Sheila Stafford, Founder and CEO of TeamSense, dives into the essentials of landing enterprise clients as a startup. She emphasizes that Net Revenue Retention is the key metric for success, highlighting the importance of customer satisfaction as a business moat. Sheila discusses the decline of email as a sales tool and her preference for modern PR strategies. Moreover, she shares insights on the significance of domain expertise and the need to address operational pain points in staffing to boost productivity, making her insights invaluable for new founders.

Eric Spett, Founder and CEO of Scalebound, shares insights on sustainable growth for CEOs. He emphasizes the importance of focusing on your primary go-to-market channel rather than spreading resources too thin. Eric discusses the pitfalls of 'shiny object syndrome' and the value of sticking with proven strategies. The conversation also dives into the significance of in-person events and community engagement, offering humorous anecdotes and personal experiences that highlight the power of authentic connections in business.

Sam McKenna, Founder of SamSales Consulting and a leading expert in social selling, joins the hosts for a lively discussion. They tackle the importance of personalization in prospecting and share tips on engaging with potential clients authentically on LinkedIn. Sam emphasizes standing out by adding thoughtful comments rather than generic interactions. The conversation also touches on the evolution of go-to-market strategies and the balance between automation and personal touch in sales, with amusing stories sprinkled throughout.

Join Maria Boulden, a seasoned sales expert with over 30 years leading sales teams at DuPont and Gartner, as she shares her energetic insights on modern sales. She humorously debunks the myth that steak dinners close deals, emphasizing the need for authentic connections instead. Maria advocates for senior leaders to engage directly with front-line sellers and adapt to today’s B2B dynamics. With stories of leadership challenges and the importance of personal relationships, she offers invaluable advice for navigating the evolving sales landscape.

Michael King, a leading marketing executive recruiter and author of "Be There When I Return," shares his inspiring journey of battling epilepsy while navigating a successful career. He discusses the importance of chasing the right companies over titles and the need for relevant experience in hiring. Michael also sheds light on how job seekers should consider company culture and growth potential. Additionally, he addresses the evolving tech recruiting landscape and emphasizes storytelling as a powerful tool for raising epilepsy awareness.

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 TakeawaysA 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.Sponsored SegmentRingmaster 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 thetransaction@samguertin.comChapters00:00 Intro06:30 Introducing Katherine Andruha11:23 Onboarding and Training Challenges19:25 Effective Onboarding Practices for B2B SaaS Companies29:05 The Importance of Confidence in BDRs30:37 The Sales Manager's Role in Onboarding33:26 Territory Ownership and AE Handover35:15 Creating a Fun and Productive Environment as a B2B Seller37:45 Pipeline Progression and Accountability42:48 The Role of CMOs in Pipeline Progression44:57 Closed Lost Analysis and Product Feedback48:01 The Importance of Phone Calls48:41 Using Swag to Engage ProspectsSign 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 AndruhaConnect with Katherine AndruhaLinkedIn: https://www.linkedin.com/in/katherineandruha/ Website: https://www.fivetran.com/ ShoutoutsDoug 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!

In a world where B2B deals involve more people than ever, growth is suffering. Nick Toman shares insights on how more sellers can actually hinder win rates. The discussion includes three key behaviors that lead to successful sales relationships and how slowing down can paradoxically speed up deals. Sales compensation's role in shaping behaviors is explored, alongside the intriguing concept of 'Headway Selling.' Plus, there are plenty of lighthearted moments, from childhood sports traumas to gnome confessions!

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 TakeawaysThere 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 SegmentRingmaster 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 thetransaction@samguertin.comChapters00:00 - Intro03:44 - The "Let Me Help You Get this Car" Story07:24 - Krysten’s Embarrassing Sales Stories13:22 - Develop a Champion, Don’t Wait For Them to Show Themselves18:39 - Examples of Asynchronous Work that Champions will Do25:58 - Champions will Bring More People to Follow Up Sales Calls32:36 - Craig Details how he Landed his First Girlfriend33:35 - Who Should be Doing Asynchronous Work Within The Buying Committee41:54 - Does Your Buyer have a Point of View on the Next Steps44:54 - Mass Email Does Not Count as Multi-Threading51:10 - Who a Champion Is and What They Will Do in The Buying CycleSign 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 ConnerConnect with Krysten ConnerLinkedIn: 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 ShoutoutsChris 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=falseScott 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!