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Revenue Jam

Business & Economics Podcasts

Most Revenue Leaders aren’t sure how to close the skill gaps across their teams. That’s why Revenue Jam brings together all different content from the team at Sales Assembly so you can learn everything from Revenue Leadership Philosophy down to tactical playbooks. With topical monthly live sessions, interviews with the Sales Assembly team, and exclusive conversations with Revenue Leaders across B2B Tech, this show is guaranteed to help you close the skill gaps across your entire GTM Team. And if you are looking to join us live every month, register for our live session “Sales & Stuff & Things” with Matt Green, Samantha McKenna, Todd Caponi, and Jen Allen-Knuth.


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Most Revenue Leaders aren’t sure how to close the skill gaps across their teams. That’s why Revenue Jam brings together all different content from the team at Sales Assembly so you can learn everything from Revenue Leadership Philosophy down to tactical playbooks. With topical monthly live sessions, interviews with the Sales Assembly team, and exclusive conversations with Revenue Leaders across B2B Tech, this show is guaranteed to help you close the skill gaps across your entire GTM Team. And if you are looking to join us live every month, register for our live session “Sales & Stuff & Things” with Matt Green, Samantha McKenna, Todd Caponi, and Jen Allen-Knuth.




Ep. 37- Using RFPs to Improve Your Sales Process w/ Brad Rosen and Tony Germinario

Show Notes: This episode discusses best practices around responding to RFPs (requests for proposals), including when to bid or not bid, managing internal collaboration, maintaining relationships even if declining to bid, and leveraging AI for efficiency and learning. Listeners can gain insights into strategically approaching RFPs. Key Discussion Points: Brad Rosen Bio: Brad Rosen is President at Sales Assembly, which provides skill development for go-to-market teams. He focuses on sales effectiveness and process optimization. Tony Germanario Bio: Tony Germanario is the RVP of Enterprise at Responsive (formerly RFPIO), a software company providing RFP and proposal management solutions. He has over 15 years of experience in sales leadership. Company Bios: Sales Assembly - Services firm focused on sales skill development through workshops, custom training, and coaching. Helps teams sell more strategically. Responsive - Software company with solutions for streamlining and optimizing RFP response and proposal processes. Enables efficiency through content collaboration and AI.


Ep. 36- Scale Through Skill, NOT Headcount l Sales & Stuff & Things w/ Matt Green, Sam McKenna, & Todd Caponi

This session of Sales and Stuff and Things discusses how revenue organizations can scale through developing seller skills, rather than solely through adding more headcount. The guests provide historical context on why sales leaders often default to hiring more, despite data showing skill development is needed. They outline essential modern seller skills like decision science, writing, active listening, and empathy. Main Discussion Points - Many sales leaders are not formally trained for their roles, so they default to hiring more reps rather than prioritizing enablement (Sam McKenna) - Throughout history, sales training and education has often declined during economic downturns, leading to more reliance on quantity over quality (Todd Caponi) - Leaders and boards often prioritize short-term results over long-term enablement due to lack of experience with previous economic cycles (Todd Caponi) - Sellers today often lack skills like writing, active listening, and intellectual curiosity that are essential for modern sales (Sam McKenna) - Foundational understanding of decision science and empathy are key for applying modern sales techniques effectively (Todd Caponi) - Sales messaging and outreach should focus on buyer challenges and perspectives, not just product features (Sam McKenna)


Ep. 35- [New Data] Why Sales Cycles in 2023 are 30 Days Longer w/ Brad Rosen, Michelle Vu, & Jonah Mandel

In this episode, Michelle Vu discusses the current state of B2B SaaS sales and customer success with Jonah Mandel of Capchase and Brad Rosen of Sales Assembly. They dig into findings from a recent survey conducted by Capchase on sales procurement in the B2B SaaS space. Key topics include increasing sales cycle length, rising customer acquisition costs, and decline in LTV:CAC ratio. Listeners can expect to learn strategies for optimizing sales processes, managing discounting, improving customer retention, and more in today's climate. Main Discussion Points: - Factors contributing to longer sales cycles and how some companies are bucking this trend - Rising CAC and how to optimize spend on customer acquisition - Managing discounting behaviors of sales teams - Turning customer success into a profit center with skills for upsell - Getting ahead of churn risk before renewal conversations Guest Bios: Jonah Mandel is the VP of Sales and Customer Success at Capchase, helping businesses grow through non-dilutive financing. He previously led go-to-market efforts at Alibaba for 5 years and worked in mobile payments at Square and ShopKeep. Brad Rosen is the President of Sales Assembly, which helps teams build foundational sales skills for greater efficiency. He previously led G2's go-to-market team for 7 years after a long career in finance. Company Bios: Capchase: Provides non-dilutive financing to SaaS companies through options like revenue-based financing and a buy now, pay later purchasing tool. Sales Assembly: Offers sales training and coaching to help companies scale through the development of foundational selling skills.


Ep. 34- Creating a Culture of Learning: How to Drive Productivity and Innovation in Your Sales Team

In this episode of Revenue Jam, Matt Green and Alex Mislan discuss how to create a culture of learning within a revenue organization. Listeners can expect to gain insights on why building a culture of learning is important, how it differs from just having coaching, and practical steps leaders can take to start fostering this culture. Key Discussion Points: - A culture of learning treats learning like a business objective - it's measured, prioritized, and resourced (02:16) - Coaching tends to be situational and deal-specific, while a culture of learning focuses on underlying skills and behaviors (08:48) - Building a culture of learning leads to greater innovation, productivity, and optimal performance from teams (04:37) - Leaders often fall back on coaching instead of building a culture of learning due to desire for immediate results and competing priorities (07:14) - Important to start with small, measurable steps - open idea submissions, increase visibility, get executive sponsorship (22:24)


Ep. 33- Creating a Positive Sales Culture: Strategies for Weekly Wins and Celebrating Success l Sales & Stuff & Things w/ Matt Green, Sam McKenna, Todd Caponi, & Jen Allen-Knuth

In this episode of Revenue Jam, Matt Green is joined by sales leaders Sam McKenna, Jen Allen-Knuth, and Tod Caponi for a monthly session discussing how sales leaders can create weekly wins for their teams. They provide insights on building a positive sales culture, celebrating the right behaviors, delivering effective feedback, and more. Key Discussion Points: - Celebrating pipeline versus quality of pipeline (05:13) - Focusing on the "so what" of your solution for the customer (05:52) - Not celebrating activities that don't lead to outcomes (08:29) - Being transparent about losses and learning from them (20:17) - Giving feedback in a way that elicits self-reflection (27:27) - Delivering feedback consistently in a 2 by 2 format (29:32) - Making feedback a natural extension of validation and recognition (37:21) - Learning from all levels of the organization (39:04) - Reinforcing positive behaviors tied to company values (43:06) - Highlighting smaller wins, not just the biggest deals (47:35)


Ep. 32- Practical Personalization Templates from LinkedIn's Sales Team l Fireside Friday w/ Jeff Rosset & Kelly Marberry

In this episode, Jeff Rosset is joined by Kelly Marberry, Sales leader at LinkedIn, to discuss deep sales, focusing on quality over quantity, and strategies for achieving happiness and satisfaction in sales careers. Kelly provides insights into tailoring outreach, building rapport, and crafting personalized messages to connect with prospects. The two also touch on the importance of finding joy in your work in order to put in the effort needed to get results. Main discussion points: - The decreasing effectiveness of mass outreach tactics (00:02:23) - Transitioning from spray and pray to more strategic, personalized outreach (00:02:06) - Putting in the time and effort to truly understand prospects' needs (00:03:12) - Leveraging networks for warm introductions (00:05:34) - Achieving happiness first to enable greater success (00:12:20) - Simple daily practices for cultivating gratitude and joy (00:13:12) Guest Bios: Jeff Rosset is the CEO of Sales Assembly, a community of sales and marketing professionals in Chicago. He has over 15 years of experience in sales and business development. Kelly Marberry is an Enterprise Account Executive at LinkedIn. She was previously with Sprout Social and helped them scale during their early growth phase. Kelly is passionate about helping sales professionals find satisfaction and happiness in their work.


Ep. 31- Building a Successful Sales Team: Tips for Founders l SaaSy Talks

Episode Summary: Matt Green, co-founder of Sales Assembly, shares his insights on building successful sales teams and developing a strong sales playbook. He emphasizes the importance of finding the right people for your team, rather than relying on big logos or established organizations. Matt also discusses the challenges of transitioning from a founder-led sale to a true go-to-market motion and the need for consistency in training and development. He highlights the shift in Sales Assembly's focus from training for job titles to training for skills, and the impact it will have on their organization. ------------------------------------------------------------ Chapters: (00:00) Mistake of founders thinking big logos guarantee success in hires (01:09) Accidental entry into sales after studying criminal justice (03:40) Sales Assembly started as a solution to common sales complaints (06:46) Importance of finding the right people when building a team (08:45) Sales playbook should be written by the first sales hire (10:28) Critical elements of a sales playbook: process, methodology, language (14:25) Onboarding new sales teams can be challenging without consistency (20:57) Hiring slower and firing quicker improves team quality (22:07) Focusing on hiring A players only is crucial for success (26:44) Revenue being seen as a team sport, but sales getting blamed in tough times (31:36) Excelling in sales as an introvert (33:06) Excitement for training for skills rather than job titles (35:31) Quick-Fire Round ------------------------------------------------------------ Key Takeaways: - Finding the right people is crucial when building a sales team, rather than relying on big logos or established organizations. - Transitioning from a founder-led sale to a true go-to-market motion requires careful planning and consideration. - Consistency and alignment towards a mission are essential for building a strong sales team and company culture. - Building a sales playbook should focus on defining the sales process, methodology, and language used in communication with prospects. - Hiring slower and firing quicker can lead to better long-term success in building a sales team.


Ep. 30- Humans vs. The Machines l Walnut #WeAreProspects w/ Matt Green, Marie Brunet, Devin Liu, & Aryeh Abramowitz

How do we keep all our tech in check? Well, that’s exactly what Walnut asked their panelists from AI21 Labs, Sales Assembly, and Uniphore during their latest #WeAreProspects webinar. And while the event was a blast, what really knocked our virtual socks off was just how many sales leaders tuned in. This shows just how important it is to ensure that AI and tech are making the buying process better and not distancing us from our prospects. It was really interesting to hear all of the practical tips our experts gave on which emerging technologies they’re currently using and when they avoid them altogether.


Ep. 29- The Art of Authenticity and Empathy in Sales l MasterSaaS Live w/ Matt Green & Alina Vandenberghe

Matt Green discusses with Alina Vandenberghe his journey into sales and the qualities that make a great salesperson and sales manager. He emphasizes the importance of empathy and authenticity in building relationships with clients and team members. Matt also explains the purpose of Sales Assembly and how they provide comprehensive training and development programs for B2B software companies. Matt concludes by sharing common mistakes salespeople make and the high-demand training topics for different roles, such as storytelling for account executives and quantifying ROI for customer success. Matt Green is a sales expert and the chief revenue officer at Sales Assembly. He has a background in criminal justice but found his calling in sales. With a focus on empathy and authenticity, Matt has built a successful career in sales and now helps sales teams improve their skills and performance through the courses and certification programs that Sales Assembly offers. You can find Matt on LinkedIn: Alina Vandenberghe is the Co-founder, Co-CEO, and CMO at Chili Piper. She started her own company before high school. Selling lipstick and tech skills she then decided to get a master's in computer science because make-up was a low-margin business. She then went on to create the first mobile products with millions of users for Thomson Reuters, Bloomberg, and Pearson. Some of them went to be keynoted on stage by Steve Jobs. She help found Chili Piper in 2016 to boost buyer engagement for cool companies like Spotify, Airbnb, Snapchat, Shopify, and thousands of others. You can find Alina on LinkedIn:


Ep. 28- Adapting to Market Dynamics w/ Matt Green & Collin Stewart

As the Chief Revenue Officer (CRO), Matt continues to work as an Account Executive (AE) within his company. Let's uncover the motivations behind this unconventional choice and discover the insights it brings to Sales Assembly's sales motion. Highlights include: Holding on to the AE role as a Founder and CRO (2:00) The Benefit of Having a Very Specific ICP (4:10) Why Not Use BDRs When You Train BDRs (8:20) AI's not about Replacement, It's About Augmentation (20:00) Specializing Sales Roles (25:12)


Ep. 27- From Rookie to Revenue Generator l Transform Sales w/ Brad Rosen & Amir Reiter

In this episode, Amir Reiter interviews Brad Rosen, President of Sales Assembly, to discuss the importance of sales training and enablement. Brad explains that Sales Assembly is a skill development platform for go-to-market teams that offers fundamental sales training to individuals at different stages of their careers. They address the challenges of creating and maintaining up-to-date training content and emphasize the need for organizations to invest in sales training and enablement early on. They also highlight the unique aspects of the Sales Assembly community, including actionable next steps, diverse thought leadership, and the opportunity for experienced professionals to contribute their knowledge.


Ep. 26- Sales Assembly Proposal Power-Up l The Closing Show w/ Tanner Lacey & Nadia Milani

Want to make your proposals better? Of course! Proposals are often an after thought but are the last thing (and sometimes the first thing) a decision-maker sees when you're selling your product. Your proposals are the last step in a closed deal. So you better make them effective. We’re discussing: - The current proposal process at Sales Academy - The proposal format and structure Tanner is using - How do they follow up after a proposal is sent - Actionable takeaways from us to improve proposals All in the name of closing more deals! Tanner Lacey


Ep. 25- The Revenue Impact of Executive Emotional Intelligence l Sales & Stuff & Things w/ Matt Green, Todd Caponi, & Jen Allen-Knuth

Have you directly addressed the economic environment with your team? Your people are stressed. They don’t feel safe. There have been 201,860 layoffs in Tech in 2023. They are worried they might be next. And a lack of psychological safety creates a negative revenue impact. Because people start looking for jobs instead of new customers. But as leaders, we have to focus on how we can create psychological safety for our teams. But how? That's what we aim to answer as Samantha McKenna, Jen Allen-Knuth, Todd Caponi, and Matt Green dive into the Revenue Impact of Emotional Executive Intelligence. Massive thank you to our sponsor Insightly - Modern CRM 🧡. Did you know that 79% of B2B Leaders are unsatisfied with their CRM... So if you're struggling to create and convert cold pipeline because you can't effectively manage your sales tools, Insightly might be the CRM you need to scale. By registering for Sales & Stuff & Things, you'll qualify for a free onboarding package to help you get started! So register for Sales & Stuff & Things & check out Insightly today!


Ep. 24- Balancing Performance and Purpose: A G2 Culture Deep Dive l Fireside Friday w/ Jeff Rosset & Michelle Vu of G2

In this enlightening episode, Jeff Rosset & Michelle Vu delve into the inner workings of G2, a company renowned for its robust culture and commitment to performance, entrepreneurship, kindness, and authenticity. Our guest shares key insights into how they maintain a healthy balance between performance pressure and their team members' individual "why" — the personal goals and motivations that drive each employee.


Ep. 23- Best Practices for Creating and Maintaining a Winning Sales Territory Plan l Closing Time w/ Brad Rosen & Dave Osborne

New and experienced sales leaders know that creating and redistributing sales territories can be a challenging task. There are numerous factors to consider – industries, geography, ideal customer profile, deal size, and more – and it’s not a one-time process. If your team operates remotely, it could be even more complex. So, how do you begin creating sales territories? How frequently should you reevaluate and redistribute them? Is it fair for the best reps to get the best books of business? In this episode, Dave Osborne from Insightly and Brad Rosen from Sales Assembly discuss effective strategies for creating and maintaining a sales territory plan that is equitable and sets your sales team up for success.


Ep. 22- Leading in a Crowded Market: Inside RFPIO’s Strategy l Fireside Friday w/ Jeff Rosset & Konnor Martin

In this episode, Jeff Rosset & Konnor Martin offers an in-depth account of RFPIO’s journey to becoming a category leader in the emerging field of response management software. Despite entering the market late, the company was able to carve a niche for itself, a success the guest attributes to two key factors: an incredible product-market fit and talented sales personnel. Konnor further explains that their continued growth strategy is built on the foundation of delivering a consistent narrative to their prospects, along with strong value selling and business cases. He provides insights into the company’s latest strategic moves towards asserting its category leadership, one of which includes consolidating its brand messaging. The discussion then shifts to the competitive nature of the current sales landscape. The guest stresses the importance of viewing competition from a broader perspective, beyond just other solution providers. For him, the competition also includes potential customers choosing to stick with the status quo, find free alternatives, or not make a decision at all. This understanding of competition has fundamentally changed RFPIO’s sales approach. In addition, he emphasizes the importance of providing solid economics behind the solution, which can help a company stand out regardless of the competitive scenario. The guest concludes by stating that simplicity and sticking to sales fundamentals are key to succeeding in a complex, competitive market.


Ep. 21- Sustaining Success- The Integral Role of Customer Success in Revenue Teams l Revenue Rehab w/ Georgie Papacostas & Brandi Starr

This week, Brandi and Georgie will tackle Sustaining Success: The Integral Role of Customer Success in Revenue Teams Georgie is a third-culture kid born in the US to Greek immigrants who grew up in the Middle East. She began her career in the public sector at the Embassy of Cyprus, conducted health care research as an analyst at the Advisory Board Company in Washington, DC., and taught English in Spain and Ethiopia. Leaping into SaaS and Customer Success in 2015, her first Customer Success role was at HubSpot’s Dublin, Ireland office, where she became a leader overseeing the Implementation Specialist team. Since then, Georgie has led more than 40 global Customer Success professionals across teams at SaaS companies of various stages, including Sprout Social, Showpad (Learncore) and Workday (ScoutRFP). Georgie has spent her entire career at mission-driven organizations and companies, consistently putting the citizen, the patient, the customer, or the team at the center of everything she does. Bullet Points of Key Topics + Chapter Markers: Topic #1 Defining Customer Success [07:01] Topic #2 The Role of Customer Success in the Revenue Process [11:37] Topic #3 Optimizing Revenue through Customer Success [17:45] So, What's the One Thing You Can Do Today? Georgie’s one thing is to “Go and find a CES (Customer Effort Score) person that you haven't connected with yet and have a 20-minute conversation with them”, she advises and ask them to share about their role. Links: Get in touch with Georgie Papacostas on LinkedInSales Assembly


Ep. 20- Closing Skills Gaps for Salespeople in 2023 l B2B Revenue Leaders w/ Jeff Rosset & Dustin Tysick

Jeff Rosset, Founder & CEO of Sales Assembly, joins Dustin on this week's episode to discuss the changes in the sales industry in 2023. In today's landscape, companies are now focusing on efficiency and structure, and sales reps need to develop skills in building pipeline and self-sourcing leads. They share advice for closing skills gaps, overcoming AI's challenges in sales and the changing roles and responsibilities of sales professionals. You can learn more about Jeff and Sales Assembly on LinkedIn.


Ep. 19- Who is Your Ideal Customer? Defining ICP and Aligning Go-To-Market Teams Around It l Closing Time w/ Brad Rosen and Chip House

Every business has its “best” customers, aka those who see significant value from your products or services, become long-term repeat buyers, and advocate for your brand. But when it comes to figuring out who those customers are and how to best serve them, alignment is key. Then, GTM leaders need to closely monitor sales metrics (such as ACV, churn, and NRR) to ensure your ICP is still relevant 6, 9, and 12 months down the road – which is especially challenging for high-growth companies looking to go upmarket. In this episode of Revenue Jam, Insightly’s Chip House and Brad Rosen from Sales Assembly talk through defining ICP (ideal customer profile) and ensuring that it resonates across your organization. Brad Rosen Chip House


Ep. 18- Top Strategy for Generating More Leads Without Annoying Emails and Cold Calls! l SaaSSales w/ Matt Green & Mor Assouline

Matt Green, CRO of Sales Assembly, will teach you the top strategy for generating leads without annoying emails and cold calls. This strategy is based on principles of prospecting that have been proven to work time and time again. If you're looking to generate more leads without annoying email campaigns or high-pressure cold calls, then this is the video for you! In this video, we'll show you how to use a simple cold calling strategy that will get you the leads you need without annoying your prospects or wearing them down! Matt Green Mor Assouline