The Revenue Architect Podcast

Most frontline sales managers get promoted into the role on the back of being superstar salespeople. So why do so many struggle to succeed in a management role? Well, it turns out that being a top sales manager takes a completely different set of skills to being a top salesperson, not least the ability to be an effective coach. Common wisdom says that it takes years of experience to become a great coach, as you need to have seen a wide range of scenarios before you can start dishing out advice. However, frontline sales managers don’t have the luxury of time as they are expected to deliver results instantly. What if there was a way to accelerate the learning process? Well, there just might be. Matt Benelli is at the forefront of solving this problem as co-founder of Coachem and shares his wisdom in this week’s podcast. From how to step back from trying to do it all yourself, to how to personalize your coaching approach for each of your direct reports, to what data to use to identify coaching opportunities, there’s a ton of actionable advice in here. It’s a must listen for anyone who is a new frontline sales manager, anyone who is managing a frontline sales manager and anyone eyeing sales management as the next step in their career. Podcast contents 0:30 Can you tell us about Coachem and the problem you’re solving? 3:50 What are the top skills gaps that you see in frontline sales managers? 6:30 Why do frontline sales managers need to step back and not try to do everything themselves? 7:30 What would you do differently if you treated each of your salespeople like the biggest deals you’ve ever closed in your career? 8:55 The 6 elements of a coaching framework: Trust, Personalized Focus, Role Modeling, Deliberate Practice, Immediate Feedback, Consistency. 12:30 Why “do it like me” is the death knell for performance. 14:00 The importance of personalized focus. 15:30 What does deliberate practice entail? 19:30 The dangers of asking too many questions without first establishing trust and credibility. 22:30 Balancing short term performance pressures with long term coaching by using data. 29:00 How to drive immediacy of feedback. 32:30 How preparation and practice improves objection handling. If you enjoyed listening to my conversation with Matt, you’ll love listening to this one from the archives with Bernadette, who recently went through the transition from AE to sales manager and shares what she learned. And if you haven’t already done so, please subscribe! Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

Outsourced procurement is one of the biggest trends sweeping SaaS right now as companies switch from a growth at all costs mindset to one of finding greater efficiency. Companies like Vertice, Vendr, Tropic and others are capitalizing on this trend by helping companies optimize their SaaS and cloud spend, through a combination of price transparency, usage tracking and competitive bidding. This is disrupting the status quo for software sales teams, especially the 55% that have historically not published their pricing and instead leaned on techniques like value-based selling to maximize order sizes. Matt Hicks is at the forefront of this trend in his role leading the global sales team at Vertice and gives us a peek behind the curtain of this burgeoning category. From how Vertice works with its clients, to what salespeople should do when they run into an outsourced procurement team during a sales process, to where this trend is taking us in the next year, there’s a ton of valuable advice in here. It’s a must listen for anyone in a software sales role. Give it a listen here or on Apple Podcasts and let me know what you think! And if you haven’t done so already, please consider subscribing. Podcast contents 0:40: Can you tell us about Vertice and your role there? 4:50: Discussing the lack of price transparency in SaaS compared to other industries. 5:45: What advice would you give a salesperson when an outsourced procurement provider shows up in the buying process? 9:25: Does an outsourced procurement provider have to secure additional discount from a salesperson to justify their value to their client? 12:20: When a client is interested in buying a piece of software, does Vertice go out and find competitive bids for similar solutions from other vendors? 16:00: The lack of standardized terms in SaaS causes a lot of friction in the buying process, especially when compared to industries where all parties . How do you see this playing out in the long term? 21:00: Outsourced procurement tends to show up late in the sales process, which frustrates salespeople. How do you educate your clients on when to bring you in? 25:00: Sounds like you are getting into the Contract Lifecycle Management space? 28:00: Discussing the chronic under-utilization of SaaS tools, especially in salestech and martech. 31:00: How did you get into selling financial services? 34:30: You describe yourself as a servant leader. How does servant leadership influence how you lead a sales team? 40:00: What lead generation strategies have worked best you over the years? Resources The Ultimate Guide to Purchasing Sales Software (Vertice) Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

Experienced marketers know that creating a new business category requires a very different approach to capturing demand in an existing category. Not only are budgets for your product yet to be created, there’s no search data to tap into for quick wins and your sales processes can be lengthy, unpredictable and expensive. Andy Singer, CMO of OpenRaven is deep in the weeds of building a new category in the cloud security space called Data Security Posture Management, helping Chief Information Security Officers understand where their data are located, what types of data are in each location, and critically, how much of each type there is — in order to apply guardrails and reduce risk. There’s a ton of valuable insights in this podcast, from how to use social listening to identify adjacent problem spaces, to why LinkedIn is better than Google for category creation, to why account-level signals are more valuable than lead-level signals, to why you need to continue prospecting an account even if after you’ve started talking to a champion. Andy also has a wealth of experience leading marketing teams and has been through economic downturns before. He shares his advice on bad habits to kick, where to focus your marketing efforts and specific tactics that have served him well during periods like these. I learned a ton from talking to Andy and I know you will enjoy listening to this one! And if you haven’t already done so, please subscribe for more great content like this! Podcast contents: * 0:50: Cheesy question to get us started :) What type of marketer are you and what is your marketing superpower? * 1:40: Tell us about OpenRaven and the problem you are solving? * 7:50: As marketer what do you need to do differently when creating a category vs capturing demand. Challenges you run into with forecasting. * 12:20: Big mistakes marketers make is positioning at the vision level. Need for listening to customers. * 14:00: When to use search vs social. How to use social for listening and attach to an adjacent space, adjacent topic. * 18:00: What are some bad habits B2B marketers need to kick in the current economic climate? * 21:30: How ad platforms use advertisers budgets inefficiently / encourage advertisers to broaden their targeting. * 25:00: Benefits of using LinkedIn for ads. Targeting. Creatives. Importance of making your target market small in order * 27:00: Importance of tight targeting and matching the creative to the targeting. * 30:00; How to use Marketing Qualified Accounts in Account Based Marketing. Measure account level score across buyer personas. Use tools like Qualified to figure out which accounts to focus on. Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

Seasoned enterprise sellers know that closed won deals have 3 common traits: * A clear champion, who stands to gain from buying the product. This is the easy part. * A collaborative plan between the champion and the salesperson to build consensus, secure approvals, navigate procurement and get a contract signed. This is also fairly easy to figure out. * A number of key internal meetings where consensus is built, approvals are secured and procurement is navigated, yet where the salesperson is never going to be invited to. This is the #1 challenge in closing deals and it’s only getting harder. A $50k deal can have 4-5 stakeholders and a $100k deal can have 10 or more. If you’re lucky you’ll end up stuck in endless meetings saying the same thing over and over again but more commonly you’ll end up managing chaotic email threads in an effort to get everyone on the same page. My friend and former colleague Brendan Weitz, co-founder of Journey is at the forefront of solving this problem. Journey enables salespeople to give their champions the ammunition they need to sell the deal internally, by using an interactive story format to engage all the stakeholders. This has given him a lens into how top performing AEs are closing deals and what they are doing right. From the content and strategies used to engage stakeholders, to how to help your champion navigate their buying process, to how to use warm intros to build pipeline 10x faster, to how to automate your LinkedIn outreach, to when to use product-led vs sales-led sales processes, there’s a ton of gold in here for any founder or early stage sales leader doing enterprise sales. I always learn something new when I talk to Brendan and I know you will enjoy listening to this one! And if you haven’t done so already, please subscribe! Podcast contents * 1:00 Tell us about Journey and the problem you are solving * 3:15 Strategies salespeople can deploy to engage stakeholders * 5:35 Figuring out your ideal customer profile for Journey * 7:30 The surprising number of stakeholders involved in a $40-50k deal * 8:50 Helping champions understand their own buying process * 9:45 Strategies that have worked best for generating leads * 11:10 Systematizing and scaling warm introductions * 14:00 Comparing the success rates of warm intros vs cold outbound * 15:30 Scaling automated outbound on LinkedIn * 18:30 Comparing the results of product-led vs sales-led motions * 20:50 Common hacks that AEs are doing to engage stakeholders * 23:10 Overcoming objections to using Journey * 28:10 The importance of multi-threading for understanding wins and losses If you liked this podcast, you’ll love these: Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

Last month, I wrote about the top 3 things SaaS companies need to plan for to be successful in 2023, one of which is finding greater efficiency in customer acquisition. If anyone knows the secrets to finding efficient growth, it’s Scott Stouffer: * As CEO of Salsa Labs, he reduced his customer acquisition cost (CAC) by 75% within his first 12 months and cut his sales cycle in half, by systematically finding and eliminating the friction in his go-to-market. * Now as CEO and founder of scaleMatters he has productized what he built at Salsa Labs so that the rest of us can realize the same benefits. In this podcast, Scott shares his strategies. From instrumenting your tech stack to collect accurate data, to avoiding multi-touch attribution and lead scoring, to focusing on channel-level performance, to making your target market as small as possible, to using sales calls to optimize your marketing messaging, there’s a ton of actionable advice in here. It’s a must listen for both marketing and sales leaders, especially in today’s climate where we are being tasked to do more with less. Give it a listen here or on Apple Podcasts or on Spotify and let me know what you think! And if you haven’t done so already, please consider subscribing. Podcast contents * 0:30 Can you tell us about scaleMatters and problem you are solving? * 3:30 What trends are you seeing in customer acquisition? * 6:50 Why do you think there’s never been a perfect way to attribute return to marketing programs? * 9:10 Discussing the many common pitfalls of using multi-touch attribution and lead scoring. * 16:00 How can marketers compete in highly competitive, saturated channels? * 21:00 How to use competitive intelligence tools like Gong and Chorus to test your messaging. * 27:30 How should marketers figure out their total addressable market (TAM)? * 29:30 What does onboarding onto scaleMatters involve for a new customer? Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

It’s every sales leader’s dream to have a team of salespeople that knows where to spend their time, builds half their pipeline through their own prospecting and crushes the competition during the buying process. Jen Bennett has made this dream a reality at multiple companies and shares the keys to her success in this podcast. From how to translate your company’s ICP into a target account list, to how to leverage your network for intros and your customers for referrals to how to decide which deals to focus on, there’s a ton of valuable advice in here. It’s a must listen for anyone in a sales leadership role, especially in today’s economic climate, where salespeople can no longer rely on marketing and SDR teams to feed them and have to fight for every deal. Give it a listen here or on Apple Podcasts and let me know what you think! And if you haven’t done so already, please consider subscribing. Podcast contents * 1:00 Can you tell us about Trulioo and the problem you’re solving? * 1:55 What do you typically try and get done in your first couple of months to ramp up as a senior sales leader? * 4:00 We discuss how customers are increasingly looking for vendors to truly understand their problems rather than to sell them a product and the importance of providing great service. * 6:00 What did you take with you on the journey from media sales to software sales and what new skills did you have to learn? * 9:10 How do you overcome competition in the sales process? * 14:30 How do you figure out customer profile and get your team aligned and focused? * 17:15 How do you think about generating leads? What strategies have worked best for you? * 20:30 Do gifting platforms work? * 22:00 How do you enable your salespeople to leverage your board and execs for lead generation? * 25:00 Why are salespeople reticent to ask for referrals? Additional reading Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

Making the jump from AE to head of sales is notoriously difficult. So is making the jump from media to SaaS. Doing them both at the same time is virtually unheard of but today’s guest Bernadette Hunter has done just that and is thriving. After a successful career as an account executive selling advertising at Microsoft, Facebook, Polyvore and Tumblr, Bernadette made the double jump from being a senior AE in media to the head of sales and customer service at a Series A SaaS startup, Flavorcloud. There’s a lot of gold in this podcast, from how Bernadette networked with her now boss over multiple years, to how she meticulously researches and tailors messaging to prospects before reaching out to them, to how she determined the company could move upmarket, to why she combined her AEs and SDRs into full-cycle reps, to how she structures high impact QBRs for her customers. It’s a must-listen for anyone looking to move into sales management, anyone looking to move between media and SaaS and a great refresher for anyone who has already made either of those jumps. I’ve known Bernadette a long time and always learn something new every time I talk to her. Give it a listen here or on Apple Podcasts and let me know what you think! And if you haven’t done so already, please consider subscribing. Podcast contents * 0:45 Can you tell us about Flavorcloud and the problem you’re solving? * 1:30 You recently made the jump from being a senior AE to managing a sales team. How did that happen? * 5:00 We discuss some of the key differences between selling media and selling SaaS. * 7:00 You recently went upmarket from mid market to enterprise. How did you figure that out? * 10:18 What does your prospecting motion look like today? * 13:05 You’re doing a lot of research and personalization in your prospecting and focusing on quality over quantity. What results are you seeing? * 14:40 You mentioned using gifting platforms in your prospecting stack. How are those are working? * 16:00 You spent a long time in B2C marketing. What can B2B marketers learn from B2C marketers? * 19:00 We discuss some of the challenges with attribution in B2B marketing and how LinkedIn is starting to address them in a similar way to how Facebook did 10 years ago. * 22:45 You switched from Hubspot to Salesforce. Why? * 26:20 You have a usage-based pricing model. What does your sales and onboarding process look like? * 29:15 What does a QBR at Flavorcloud look like? * 31:45 What does your go-to-market team look like? Additional reading How to land your first management role and develop the skills to succeed in it What SaaS sales leaders and media sales leaders can learn from each other Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

This week I had the huge pleasure of chatting with one of my subscribers, Kit Wetzler, VP of Sales at data observability platform Bigeye about what he’s learned from being the first sales leader at a number of startups selling to technical buyers. Kit is an absolute gold mine of insight and advice for early stage sales leaders. From how to figure out if a founder is a good fit to work for, to what needs to change when taking over from a founder-led sales motion, to defining sales processes that keep deals moving forward, to using mutual action plans to get through complex POCs, to hiring the right profile of account executive, to coming up with a plan that’s achievable, to partnering with product to sell and deliver on the future roadmap, and much, much more. Its a must-listen for anyone looking to jump into a sales leadership role at an early stage startup, as well as a handy refresher for anyone who is currently in the role. I personally learned a lot from speaking with Kit! Give it a listen and let me know what you think! And if you haven’t done so already, please consider subscribing. Podcast Contents 0:25 — Tell us about Bigeye and the problem you’re solving 1:00 — You came up through big companies like Citrix and Amazon. How did you transition into early stage sales leadership? 1:55 — What lessons have you learned from taking over from the founder as head of sales? 3:30 — Which processes do you build first? 7:15 — How do you structure a proof-of-concept (POC)? 9:05 — How do you stop POCs from going sideways? 12:10 — How do you keep stakeholders engaged during a POC? 13:35 — How do you prospect technical buyers at an early stage company? 18:20 — What does the initial team typically look like and how do you grow it? 21:35 — What should founders look for in their first sales leader? 24:15 — What are the biggest things first sales leaders get wrong? 26:00 — How do you figure out if a founder is a good fit for you? 28:10 — What advice would you give on coming up with a plan that’s achieveable? Additional reading How to build your first sales playbook How to empower your product team to unlock revenue growth The 4 reasons heads of sales fail (and what to do about them) Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

This week I had the immense pleasure of chatting with one of my subscribers, Justin Schweisberger, CRO of contract management platform Pramata about how he’s built their go-to-market motion. Justin is big on using process and data to inform his decisions, which has helped him execute a shift from doing complex outbound sales across multiple stakeholders to simpler inbound sales with a consolidated buyer in legal ops. He also took a non-traditional route to being a CRO, coming up from law school via consulting and product, a journey that has heavily influenced how he approaches his role. From how he created a webinar that broke Zoom, to how he qualifies buyers, to how he deals with investor pressure, to how he handles buyer objections: there’s so much gold in this podcast I’ve personally learned a ton! Please give it a listen and let me know if you’d like to hear more real world stories like this. And if you haven’t done so already, please consider subscribing! Podcast contents: * 0:15 — Can you give us a primer on Pramata and the problem you are solving * 1:10 — You took a very non-traditional career path to becoming a CRO. Can you tell us about your journey? * 3:20 — How has your experience shaped how you solve problems as a CRO? * 6:00 — How did you figure out who your ideal customer profile is? * 8:25 — Legaltech is a fairly new category in SaaS. How ready are they to buy? * 12:15 — How do you qualify where buyers are in their journey? * 14:50 — What strategies are working for you in generating leads? * 17:10 — How do you handle leads that aren’t ready to buy? * 18:30 — Dealing with investor pressures. * 19:30 — What objections do you run into and how do you overcome them? * 23:30 — How has your GTM team grown over the years? * 26:00 — How going downmarket and simplifying the product actually led to more enterprise deals Helpful resources: * How to adapt your sales process for inbound vs outbound * What to look for in a CRO Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe

This week I had the pleasure of chatting with one of my subscribers, Abeed Mohamed of Birdie, about how he built their go-to-market motion over the last 5 years. From day one in a startup incubator sending cold emails to prospects to the present day as Chief Commercial Officer of a 100+ person company with $50M in venture funding, Abeed’s journey is a case study in doing founder-led sales, packed with lessons that any early stage sales leader will find incredibly useful. Contents: 0:30 — How did you get the idea for Birdie? 4:30 — How did you find your first customers? 6:20 — What kind of objections did you run into in the early days? 10:00 — How long did it take you to figure out your ideal customer profile and value prop? 12:10 — Looking back, what are some things you got right along the way? 15:20 — How did you generate leads? 21:00 — How has your team grown along the way? Get full access to The Revenue Architect at www.therevenuearchitect.com/subscribe