SellingSherpa

B2B Sales Best Practices

Revenue Builders (podcast summary)

The Power of Belief with Dean Otto – Nov 13, 2025

(skipping since not a revenue leader)

Leading from the Front: Building Credibility at your SKO – Nov 6, 2025

  • SKO Resources from Force Management
  • SKOs need to be all about training reps how to sell better by putting their best peers on stage. “Get what good looks like up on the stage.” – McMahon
    • Why are prospects taking calls? Who in our organization is the best as cold calling, sending emails, and sending LI messages?
    • How do I build a champion?
    • What do I talk to the economic buyer about?
    • How did you determine the ICP?
    • Who is the best at getting and using customer references?
    • Who is the best at running first meetings?
    • What are our top 10 use cases? Which reps are best at selling each of them?
  • Reference to: Marty Carty
  • Knowledge
    • ICP
    • Value prop for ICP
    • How does my buyer buy? How will we engage?
  • 4 essential questions:
    • What problems do we solve?
    • How specifically do we solve them?
    • How do we solve them differently than anybody else?
    • Where have we done it before (with points)?
  • Leaders and managers should role play first. Don’t ask others to do something you would not do.
  • Key skills for sellers
    • Attaching to the biggest business issue facing a customer
    • Influencing decision criteria with your company’s differentiation
    • Being a voracious qualifier
    • Listening, asking great questions, then confirming

Creating Adaptive Sales Playbooks with Dan Fougere – Oct 30, 2025

  • Reference to
  • PLG signals:
    • Download the product
    • Looking at the user manuals (documentation)
    • Development and testing
  • Open source to paid
    • Service level agreement (SLA)
    • Hosting
  • PLG companies should build [sales-led enterprise outbound] before they need it. – Fougere
  • If you raise prices, go out and speak to your best customers and explain how you have invested in specific innovations that add value for them
  • Kaplan’s “Tentpoles”
    • ICP
    • 4 Essential Questions of Value (1) What problems do we solve? (2) How specifically do we solve them (3) How do we solve them differently than anybody else? (4) Where have we done it before (with points)?)
    • Engagement model
    • AE success profile
  • Sales leaders – you don’t [reactively] go where [your reps] ask you to go. You [proactively] go where you are going to have the biggest impact on your own success. – Fougere
  • Fougere’s desired traits:
    • Intelligent
    • Intellectually curious
    • Ambitious
    • Open to learning / adaptable
    • History of career progression to better and better companies and in better and better roles
  • When hiring leaders, ask, “Who are the best people you have hired?” & “Who are you going to bring with you?” Then probe:
    • Why did you hire them?
    • Why do you say they are the best?
    • How do they compare to the people on your team right now?
  • When you win a deal, ask the buyer: [Kaplan]
    • Where were we better than we think we are?
    • Where were we not as good as we think we are?
    • Who would you have bought from if they had a better product?
  • Dan’s operating rhythm:
    • Mon: 1:1s
    • Tue/Wed/Thur: Maximum surface contact with customers – PG, etc.
    • Fri: Forecast rollup
  • I’d rather my sales leaders spend most of their time in customer meetings at the front end of the sales process.
  • AI use cases: forecasting; enablement; PLG buying signals

Leadership, Generational Insights, and the Power of People with Susan Lucia Annunzio – Oct 23, 2025

(skipping since not a revenue leader)

Driving Sales Behavior with Effective Compensation with Jose Fernandez – Oct 16, 2025

  • “If you want to change the behavior of a sales team, you change the comp plan.” – Fernandez
  • Gate example: Accelerator contingent upon landing at least 4 new logos at $100K or more.
  • “Your comp plan should be so simple that reps don’t have to write it down.” – McMahon
  • Late comp plans are a huge demotivator. Start reviewing your comp plan 3 months before the start of the fiscal year so that you can launch on Day 1. Pressure test each iteration by asking reps and leaders how they will ‘game the plan.’
  • Back-test new comp plans to see how they would have performed if in effect the prior year.
  • “Keep a ‘SPIF bucket’ of ~10% of the compensation budget in reserve to create incentives for unplanned incentives such as recognition, selling products from newly acquired companies, etc.” – McMahon
  • “Having over-performers make a lot of money is the best recruiting tool I ever had… you don’t need to pay a lot for recruiting… they are knocking my door down… they are coming after me.” – McMahon
  • “Great reps are not going to join your company if you have a cap in your comp plan.” – McMahon
  • “Forecasting in a consumption model is an analytical exercise, not a rep exercise.” – Fernandez

The Power of Gratitude: An In-Depth Discussion with J. Douglas Holladay – Oct 9, 2025

(skipping since not a revenue leader)

Resilience in Sales Leadership; Steve Garraty’s Journey from Cancer Survivor to Successful Leader – Oct 2, 2025

(not a sales discussion)

Navigating Energy Challenges and Innovations with Carl Coe – Sep 25, 2025

(not a sales discussion)

Scaling Success: Revenue Growth and AI with John Schoenstein – Sep 18, 2025

  • Hiring traits
    • Intelligence
    • Competitiveness (in a ‘team sport’ environment)
    • Coachability / Adaptability
    • Curiousity
    • Act with a sense of urgency
  • Ask candidates, “What are three things you like about your current situation and three things that give you pause?” and be leery if they answer, “the number of leads coming in.” – Kaplan
  • Diagnostics
    • Bookings per AE (overall; by region; for ramped reps; for ramping reps)
    • Deal size (average and median)
    • Bookings (and logos) from new and from expansion
    • NDR
  • Hire incremental AEs in regions where productivity is strong and growing

Mission Driven Leadership with Mike Hayes – Sep 11, 2025

(not a sales discussion)

A Masterclass in Closing Big Deals with Steve Waugh – Sep 4, 2025

  • If you have superior delivery/implementation and in an RFP-driven sale, suggest to your champion they they include a required penalty for not delivering by a specific but aggressive date. Example, 25% penalty per day if not delivered by day 5 after the order is placed.
  • When selling large deals, you need to shift prospects from thinking about cost to value.
  • Focus on the C-suite first then go wide and understand your champions, neutrals, and detractors.
  • “Detractors show up as wolves in sheep’s clothing. They will meet with you, they will smile, they will pat you on your back and they will cut your throat when you are not looking.”
  • Champions rise to the top. Neutrals vanish. Detractors move to the side despite your efforts to win them over as champions. You have to isolate them and keep your eyes on them.
  • A mid-to-senior level person who lobs challenging, competitor-friendly, irrelevant, or out-of-context objections in group meetings is likely a detractor.
  • To surface detractors, search to see if who has provided case studies, testimonials, or webinar appearances for your competitor.
  • Your most likely detractors are people who served as champions for the incumbent solution. If you knock out ‘their’ solution, they suffer a personal loss and will very likely leave the organization.
  • “I’m confused, I’m giving you $500M of ROI for $15M of cost… maybe we are not the right solution for you. I’m telling you want I can do; if you have a better solution, what is it?”
  • Calculate ROI using your economic buyer’s team’s numbers [not your estimates.]
  • Even if it is accurate, you may need to tamp down your ROI if it seems crazy-high to be closer to your prospects target internal IRR. Or, if they don’t believe it, then say, ‘We used your people’s numbers but OK, let’s cut it in half. That is still a lot of value.’
  • If buyer’s don’t believe the ROI (but you do), then offer performance based pricing where they would pay you if certain key metrics are achieved. This gets them to calculate the potential cost and makes it more likely to accept your fixed cost proposal.
  • If you go big, you can always move down. But, if you start small, you can’t go up.
  • Big deal people referenced: Marty Carty; Mark Musselman; Jeremy Duggan
  • Big deals often require changes to your company and your product
  • Senior executives buy risk-adjusted ROI, not how you accomplish it. Proof that you have delivered to others in the past is critical.

Scaling Sales Operations with Meghan Gill – Aug 28, 2025

  • MongoDB created an internal tool (Argos) to enable decentralized territory management by field sales leaders. The system includes a per-account TAM estimate.
  • “The fewer accounts you have, the more productive you are.”
  • “Go with named accounts from the get-go rather than assigning geographic territories and leaving it to reps to figure things out.”
  • KPIs
    • Sales productivity (by tenure; by segment; by geo; etc.)
    • Average total meetings and new business meetings per rep per week
    • Qualified pipeline creation (moving from Discovery to Scoping)
  • Management operating rhythms
    • First line managers: pipeline generation and recruiting
    • Mid-level managers: forecasting
    • Executives: planning
  • RevOps people need to trust but verify
  • At least at one point, MongoDB paid reps at the end of each quarter based on the greater of the annualized run rate or the commitment. If the run rate increased, they would get paid incrementally. If the run rate decreased, they would have a clawback.
  • You can’t manage everything in a comp plan; keep it simple with one to two elements.

Empowering Leadership: Persistence, Adaptability, and Self-Awareness with Tom Heiser – Aug 21, 2025

(skipping since not a sales-centric discussion)

Mastering Asia-Pacific Market Entry with Andrew Robert Clark – Aug 14, 2025

  • You cannot treat Asia-Pacific as homogeneous; you need to localize by country.
  • When entering a new country in APAC, be prepared to invest for 2 years. The minimum viable local team is a country manager, support, channel, marketing, direct sales, and SDRs.
  • You can start immediately in Australia.
  • The first three hires are AE, SE, and tech support.

Spotting the Will to Work Hard with Carsten Neuhaus – Aug 7, 2025

(skipping since not a sales-centric discussion)

The Power of a Playbook with Steve McCluskey – Jul 31, 2025

  • Key metrics:
    • Rep metrics: POVs; EB meetings; time to get back on site after 1st meeting
    • Deal metrics: ASP; sales cycle; win rate
    • Business metrics: expansion velocity
  • “The average rep can do 90-100 quality meetings [per year]” – Steve McCluskey
  • Hold your 1st line and 2nd line leaders accountable to the time it takes new reps to get their first deal. – John McMahon
  • If you can get new reps through their first two sales cycles, then they will know what they are doing. – Steve McCluskey
  • I training my salesforce to make sure they can: scope right; get a champion; get to the EB; prepare for the EB meeting; execute the EB meeting; prep and execute a POV. – John McMahon
  • A lot of CROs get clouded by so much data that they cannot really see what is going on in their organizations. – John McMahon
  • Rep churn [which cascades into recruiting delays and ramp time] is the number one killer to the bookings number. When reps leave, probe [1st & 2nd line] managers deeply on what went wrong. – John McMahon
  • We always had 4 days in the field. As a first line leader, I made 10-15 sales calls per week. – Scott McCluskey
  • The second line manager needs to be held accountable to rep recruiting and rep development. – John McMahon
  • Ask reps to focus on no more than 3-4 metrics. Nothing else. When you give the more than they can remember, you start to paralyze people. They should not have to write it down. – John McMahon
  • People referenced: Jeremy Duggan; Paul Cant; Andy Sadler; Tom Levey; Peppa Wise; Noah Stevenson; Luke Rogers;

The Critical Role of Sales Managers in Driving Growth with Scott Rudy – Jul 24, 2025

  • The job of a first line sales manager is to attract, develop/coach, and retain top talent.
  • Second line managers must focus on quality:
    • Assess AEs then inspect & discuss the development plans of AEs with FLSMs
    • Remain actively involved in AE recruiting and hold FLSMs accountable to hiring standards
  • “You want to get promoted? Show me who you recruited and personally developed to take your spot. If you can’t, you won’t get it. Done.” – John McMahon
  • ‘Sales leaders need to spend time developing every rep on their team – not just riding along with top reps on marquee deals.’ – John McMahon
  • “Every time you lose someone, run a talent loss review. Bring in the recruiter, the HR business partner, the first line manager, and the second line leader. Ask four questions. Did we hire the right person? Did we onboard them successfully? Did we coach them consistently? What else can we learn so that this never happens again? I wanted us to feel guilt and pain and agony that we make this hire and thought the person was going to be great and, in the end, we let them slip away.” – Scott Rudy
  • Don’t just create job descriptions, define success profiles and consistently hire to them.
  • First line managers who come in from outside the company need extreme focus and urgency on learning the product and its differentiators.
  • Even if you don’t have open headcount, continue to interview to find A-players. If you find someone exceptional, be prepared to exit an average performer. – John McMahon
  • First line managers always have three openings on their team because one person will get promoted, one person will be terminated, and one person will surprise you and leave. – John Kaplan
  • You always need a full time or you are at risk of getting behind on your number. – Scott Rudy
  • Reward people who are great at bringing in great talent. – John Kaplan
  • When hiring, it is not just whether someone can do something. It is whether they have the energy and the drive to do it. Will they get energy from the specific work they are doing? People can fool you and fool themselves. What are the three things you loved most about your favorite job? What are the three things you hated about your worst job? Who was the best manager you ever had? Why? The worst? Why? – John Kaplan

The Role of Emotional Intelligence and Authentic Leadership in B2B Sales with John True – Jul 17, 2025

  • During the middle-to-late part of interviews, I first ask, “How do you think you are doing?” Then, I follow with, “How do you know?”
  • In a qualified opportunity, get face-to-face as soon as possible, especially with the economic buyer.
  • You’ll communicate much more effectively when you know your social style and that of person with whom you are speaking.
  • Great sellers are able to go past ‘concern’ to a prospects true ‘interest.’ It takes trust to do this which is much easier in person. This is same as going past surface pain to (quantifiable) (negative) business impact.
  • Be present
  • Authentic curiosity. Interested is interesting.
  • Ask 2nd and 3rd level probing questions.
  • Genuine interest in helping others succeed. When identifying potential managers, look for reps who help others without being ask to do so.
  • Great sellers have a high degree of confidence in themselves and their solution. They don’t take things personally.
  • As a manager, seek 360 feedback by regularly asking: What do you most like about working with me? What do you most dislike about working with me?
  • Look for consistency in the types of companies a candidate is interviewing with. – McMahon
  • Great manager help people get to places that they could not get to on their own.
  • People confuse position (title) with opportunity. – McMahon
  • It is a red flag when a new leader comes in and nobody follows them.

Achieving Excellence in Leadership with Kara Gilbert – Jul 10, 2025

(skipping since not an interview with a revenue leader)

Developing a Performance Mindset in B2B Sales with Joe Eskenazi – Jul 3, 2025

  • Performance mindset (elite goal achievement) vs. knowledge management (knowledge acquisition)
  • Discovery call preparation:
    • What is the prospect trying to accomplish?
    • What do we want?
    • Who is in the meeting? What are their personal & professional wins?
    • Who do we bring to demonstrate credibility?
    • What are we worried about / where are we exposed / what could do wrong?
  • Potential champions need strong trust and motivation to introduce you to the economic buyer.
  • Prepping reps (McMahon)
    • Elevator pitch
    • 10 most common objections
    • how we drive value
    • what landmines competitors will lay against us
  • It is tempting to take a champion at their word so you can ‘check the box’ on MEDDPICC criteria. However, you must trust but verify by testing your findings with multiple people in the prospect account.
  • Prospects will tell you their position, but not their interest. When you encounter resistance, for example hesitation to take you to the economic buyer, ask yourself, “Why?” Moreover, ask you prospect ‘why’ with authentic, confident curiosity. — Kaplan
  • Intuition comes from experience and experience comes from practice. – Kaplan

Mastering Sales Leadership with Eric Erston – Jun 26, 2025

  • Sales process, messaging, qualification methodology, and forecasting are all intertwined.
  • 3 attributes of a champion: [Kaplan]
    • power and influence
    • actively selling on your behalf
    • they have a vested interest in your success
  • If it is ‘out there’ in the digital world, sellers should expect that prospects will expect that AEs have consumed that information. – Kaplan

AI-Driven Sales Innovation with Bobby Morrison – Jun 19, 2025

  • Pods by geo & industry: solution engineer (SE); partner development manager; sales rep (AE); launch engineers (CSM)
  • AEs are the primary owners of industry domain expertise (at Shopify)
  • SEs have a critical responsibility to capture and share product gaps. Gaps are either addressed via internal development, ISVs, or partners.
  • Shopify hires partly based on Life Story [JD: related to TopGrading]
    • Learning agility
    • Curiousity
    • Strong beliefs, loosely held
  • Shopify has Chaos Monkey – every two years, they wipe out your email, your Slack channel, and your calendar (other than customer facing meetings)
    • This forces prioritization
    • Only about ~30% of internal meetings come back
  • Shopify has an expectation that managers build AI solutions for themselves and their teams
  • Revenue AI use cases fall into 3 categories. Solving for a:
    • Task: account overviews; sentiment
    • Craft
    • Orchestration

[Placeholder]

Revenue, Retention, and Recruiting with Mike Earnest – Mar 6, 2025

(Spotify) (Apple)

  • You need to constantly recruit because:
    • Someone will get promoted
    • Someone will leave you (regretted)
    • You’ll exit someone (non-regretted)
  • The number one thing I look for when hiring sales leader is their ability to recruit and retain the best people
  • Make ‘deposits’ when recruiting people by asking to learn about them and exploring way to help them.
  • Sought after hiring traits: grit (doing the hard things when no one is watching), curiosity, intelligence, coachability, and character. To understand traits, you must delve into past experiences.
  • You don’t get anything out of a having a candidate deliver a practice pitch. Sales people are great actors and they can easily memorize your pitch. Instead, we give the accounts that will be in their patch. We ask them to prioritize the accounts and identify target individuals. Last, the need to come up with discovery questions that marry our technology to the business problems the companies have. They only have a couple days to prepare for this.
  • When I’ve mis-hired, it was not because people hadn’t done it or couldn’t do it. The problem was that they did not really still want to do it. People need to be in jobs that give them energy. – John Kaplan
  • When hiring people, try to sell them OUT of the job. Walk them through how hard it is going to be.
  • Do the rounds and ask your team, give me two things you love about this job? Now, give me a couple things that are bugging you or are giving you pause? The latter are the tell-tale signs of what will be future surprises if not addressed.
  • See how people react to, “I don’t really think you’ll be able to do the job here.” – John McMahon
  • When thinking about hiring someone, ask ‘What’s the risk?’ relative to the hiring profile. The next questions are, ‘OK, how do we cover those risks? Do we have training to help? Does the hiring manager have that skill set and the ability to coach them?’ If you don’t have the resources to cover the risk, then they are not a good fit for your company at that time. – John McMahon
  • You have to be super-defined when sourcing (passive) candidates. I want someone who has been in a job for at least 4 years and has been promoted multiple times. Played sports. Has been well trained. Is a member of the ‘PTC family tree.’
  • Every week, each leader needs to send 3 messages to passive candidates in your territory. Invite them to coffee, to lunch. Don’t positioning it as a recruiting call, esp. since you may not currently have an opening. Just say, ‘I heard you were really good and I’m just trying to network.’ Those A-players are not on the market. – John McMahon
  • New hires are a great source of A-player candidate. – John Kaplan
  • When interviewing candidates, ask, ‘Where do you rank?’ OK, #2. For the next interview, bring me a printout that shows me you ranked #2. Homerun! Now, I know who the #1 and #3 are. – John McMahon
  • When hiring sales leaders, we ask them to identify 4 or 5 specific people they intend to recruit to fill openings on their team. Then ask, ‘Why these specific people?’
  • People stick around when you help people develop new skills and help them get themselves to the next level. – John McMahon
  • One of a leader’s greatest traits is helping people see themselves in the future. – John Kaplan
  • If you want the next job, act like you already have it and look for opportunities to do it.. – John Kaplan
  • 2nd line sales managers should be responsible for: (not exhaustive; John McMahon)
    • Assessing the skills, knowledge, and traits for the reps
    • Helping with rep recruiting
  • The best sales managers and leaders set a small number (2-3) of simple expectations that don’t change over time. – John McMahon

Sales Management: Key Responsibilities that Will Make or Break Success – Oct 24, 2024

  • Sales rep – Meet & exceed individual quota by:
    • Prospecting to consistently build pipeline with a clear rhythm:
      • 4-2-2 in month 1: 4 hrs/day researching and prospecting to build pipeline; 2hrs/day qualifying active deals with technical deep dives, PoVs, etc.; 2 hrs/day building the territory by meeting strategic partners, documenting customer case studies, etc.
      • 2-4-2 in month 2
      • 2-2-4 in month 3
    • Qualifying
    • Deeply understand the product so they can tailor solutions that attach-to/solve the biggest issues/problems facing customers.
    • Understand how you differentiate against the competition to position critical capabilities as required decision criteria
    • Able to articulate value at different levels of the organization spanning from technical champions to senior executives.
    • Closing deals by winning the stages
      • Manage the ‘engagement model’ of who is doing what, when, including the prospect. The engagement model is the sales process mapped to the prospect’s buying process.
      • Multi-threading
    • Building & maintaining customer relationships
    • Collaborating with cross-functional team members (marketing, product, etc.)
    • Keeping CRM up to date
    • Take the value proposition into the marketplace and get into a “3 foot conversation” with prospects
  • 1st line manager – Meet & exceed their team quota by:
    • Recruiting, developing, training, and retaining a team of 5-7 A-player reps
      • They should use an ideal candidate success profile which includes critical competencies such as territory development, building champions, etc.
      • If you are going to exit a person, it should also be based on the success profile
      • A-players are usually not actively looking for jobs
      • Regretted and non-regretted attrition are both expensive
    • Fairly and equitably dividing territories
      • A major mistake is giving the dregs of the territory to incremental hires rather than rebalancing
    • Handling escalations from the rep (often related to implementation or product issues)
    • Qualify deals when they are with and especially when they are not with their reps to determine the status (ex: timing) of the deal
      • Be a voracious qualifier so you can help your reps get unstuck either through coaching or direct engagement with prospects
    • Ensure the revenue operating rhythm is being followed on a daily, weekly, and quarterly basis
    • Accurately forecast bookings for your team
      • Knows the deep details on the major deals (above $x) they have in their forecast
    • The 1st line manager should not operate as a ‘super-rep’ since that means AEs will not be developed
  • 2nd line manager – Meet & exceed their quota by:
    • Recruiting, developing, and training a team of A-player 1st line managers
      • Coaching 1st line managers on recruiting reps
      • Help 1st line managers analyze each rep. Identify where reps getting stuck in the sales process and what knowledge & skills do they need to succeed. Create individual development plans based on this analysis.
      • The 2nd line manager should be intimately knowledgeable about the capabilities of their 1st line managers and the reps under them.
    • Need to be great at helping reps & 1st line managers get higher inside of prospect organizations via executive alignment
    • Accurately forecast bookings for their team
      • Knows the deep details on the major deals (above $x) they have in their forecast
  • 3rd line manager / VP Sales / CRO – Meet & exceed the company number by:
    • Ensure high sales productivity & efficiency
    • Analyze what is working & not working (in partnership with the head of RevOps)
    • Meet overall headcount goals on time
    • Allocate quota & quota capacity across segments as one would manage a portfolio to maximize yield
    • Understand trends and drive long-term growth strategies
    • Overseeing broader sales operations
    • Driving strategy
    • Recruiting, developing, and training a team of A-player direct report leaders
    • Implementing new sales methodologies, processes, and technologies
    • Manage P&L (occasionally)
    • Play an integral role on the executive team as a partner to the CEO, CMO, CCO, and CPTO
    • Be an available and motivational communicator
  • Critical metrics at all levels:
    • sales productivity
    • quota attainment
    • # new logos, ASP for new logos
    • # upgrades, ASP for existing customers
    • GRR, NRR, logo churn
    • Recruiting and attrition

Optimizing a Customer Success Team with Sasha Anderson – Sep 26, 2024

  • CSMs need to choose a major. CSMs get in trouble when they are not focused on either the technical side or the commercial side.
  • You tend to see technical CSMs [TAMs] for solutions that are complex, multi-product, and/or consumption-based.
  • [Post-sale, assign accounts to maximize the overlap between CSMs and AEs.]
  • Don’t let your customers ‘feel’ your org chart.
  • [Ensure there is meaningful if not complete overlap in sales and customer success compensation plans.]
  • Leading indictor metrics
    • Meetings (esp. on-site)
    • MAU
    • Expansion pipeline
    • EBRs
    • Product usage
    • Time to value
  • Customer success needs a strong operating cadence [and complementary health/value inspection methodology]
    • Weekly forecast reviews of upcoming renewals (CQ & NQ)
    • Is hygiene up to date?
    • When is the last time you met with them?
  • Run regular at-risk account reviews
  • Run internal QBRs for CSMs. Reflect on NDR, CSAT, and time-to-value.

Building a Strong Sales Team: Recruitment, Interview, and Onboarding Best Practices with Marcy Stoudt – July 11, 2024

  • Hold managers responsible for the success of the reps they hire – McMahon
  • To find great reps, ask your customers about the best sellers they buy from
  • Hiring managers need to be exceptional at selling job opportunities to candidates – McMahon
  • When interviewing an AE candidate, ask them about the best seller in their company. Listen to how they speak about the person. If they focus on things reps don’t control, such as territory, then that is a red flag. – John Kaplan
  • Don’t promote first line managers who are poor at recruiting. In fact, consider demoting or exiting them. – McMahon
  • Choose jobs based on the opportunity, not the title / position / equity. – McMahon
  • Everything else in hiring is irrelevant if you don’t have a profile based on the skills and traits of your top sellers. – McMahon
  • Interview questions:
    • What was the toughest thing you have ever done? How did you overcome it? – Kaplan
    • What was your biggest failure? – Kaplan
    • Who because of you is better? – Stoudt — esp. listen for examples of customers they impacted
    • What was the most competitive situation you were ever in? – McMahon
  • If you have an A-player candidate in your office, put an offer letter in front of them before they leave. – McMahon
  • Start onboarding new hires as soon as the sign the offer letter. – Stoudt

Evolving from Management to Leadership with Jeremy Duggan – May 7, 2024

  • A manager want the work to be great; a leader wants the people to be great.
  • You can’t lead if you don’t understand what great looks like.
  • John McMahon painted a vision that PTC would be the more feared and respected sales organization in the world.
  • Set the stage with purpose and passion – Kaplan
  • Ask: What would I do differently if I had to achieve x?
  • success = vision x belief x plan x disciplined, day-to-day execution
  • People mentioned:

The Impact of AI on Sales with James Underhill – April 11, 2024

  • AI is most helpful for accelerating administrative work and research so that AEs can focus more time on the human work of engaging prospects & customers. [Underhill]
  • Reps must build relationships, do homework on corporate goals, building cost justifications, influencing decision criteria, understanding politics, and buyer motivations. These things require human interaction and are beyond the scope of AI. [McMahon]
  • Predictive AI is great for account prioritization. [Underhill]
  • AI does not replace managers; rather, it is a tool to support better decision making. [Underhill]
  • AI should allow managers to operate with larger spans of control. [JD thought as I listen]
  • AI cannot replace critical thinking, curiosity, and hunger/persistence. [Underhill]
  • Provide reps with an AI trained on your product documentation so they are better equipped to answer questions and will consequently build greater trust with customers. [Underhill]
  • AI-based outbound will generally look the same. This will disengage buyers from digital messaging and make warm introductions even more valuable. [Underhill]
  • We [MongoDB] have a tool that allows CSMs to engage customers with, ‘Hey, we noticed that you’ve done x and y but you have not yet taken advantage of z. Should we hop on a call so I can show you how to do that?’ [Underhill]

The Path to Sales Leadership: Lessons Learned at Each Management Level with Carl Cross – Jan 18, 2024

  • (McMahon) Second line managers are responsible for teaching the first line manager how to:
    • Recruit
    • Analyze rep skills and and knowledge
    • Train reps
  • (McMahon) For reps to be successful in your company, you need to hire right, coach right, and lead right.
  • As a CRO, the last thing you want to do is get behind on your hiring plan.

Three Traits of a Successful Revenue Partnership with Alan Chhabra – Jan 14, 2024

  • Evaluate a potential partnership based on 3 customer benefits?
    • Will the partner help deliver and support our software better?
    • Does it help the customer have an ecosystem of tools that work with my software so they can build solutions faster?
    • Does the partner help my customer procure our software in all parts of the world?
  • You need resellers to go-to-market in the public sector and in Asia.
  • I don’t believe in marketing-only partnerships.

The Startup CEO with Jeremy Burton – Jan 11, 2024

  • Optimism is a force multiplier in a startup.
  • The engineering team should build what the sales team feels the big blockers are. That being said, sales should tell the engineers the problem and let the engineers solve it rather than telling them what HOW to solve the problem or WHAT feature to build. [22:00 & 36:00]
  • In large enterprise, it is harder to get meetings but the value proposition is stronger

Loyalty and Culture with Hollie Castro – Jan 7, 2024

(This was a short HR related conversation, not directly GTM)

Business Value Assessments: Looking at Opportunities through a Value Lens with Doug May – Jan 4, 2024

  • At the beginning of the sales process, slow down to speed up
  • The process the customer has typically requires some form of financial justification. If you cannot provide it, you leave it up to two other people – the customer has to do it on their own or your competitor is going to do it and box you out. [8:12-8:32]
  • Discovery does not stop when the customer tells you they have a project that needs what you sell. When that happens, the salesperson gets the happy ears because they have been taught to go find projects. Keep swinging the axe. Why do you have that project? Who sponsored that projects? What business problem does it solve? Keep digging until you find links between your critical capabilities and the challenges the customer has. [13:00-13:57]
  • If someone asks you about a feature, answer and follow with, “Why does that matter to you?”
  • If you start pushing product early on, you instantly lose credibility.
  • John Kaplan on meeting structure [36:14-37:38]
    • Purpose: The purpose of the meeting is…
    • Process: Here is what I’m going to take us through…
    • Payoff: And the benefit to both of us is…
  • The definition of a business is that it is a reason for change.
  • Purchasing does not want to be the cause of failing to achieve a strategic initiatives [56:03-58:04]
  • 3 key sections of the BVA:
    • List of all people you met (dates, names, titles)
    • Quotes about the current state and/or your solution
    • The (negative) business impact of a single specific incident the prospect experienced

Driving Sales Productivity with JP Bolen – Dec 2023

Apple: https://podcasts.apple.com/my/podcast/driving-sales-productivity-with-jp-bolen/id1610203369?i=1000637811103

Spotify: https://open.spotify.com/episode/3zkhZb8O82WFisSpJeBXUb

  • The single most important metric inside of a company is sales productivity. The leverage is who you hire, how you onboard them, and how you keep them successful and confident.
  • ‘Training sessions should be run by salespeople and sales leaders – people who are doing the job.’
  • Are you conversationally fluent on the problems we solve? (Supported by customer stories.)
  • Nine, week-long classes. One class from each track is taught each week.
    • Teach the subject at 8am on Monday.
    • Give participants a specific assignment to apply the lesson.
    • Come back on Friday to share examples and validate.
Track ATrack BTrack C
Class 1Save the DataNew Business Meeting PrepChampions
Class 2Pipeline Generation (PG)MessagingBuilding & Using the 3 Whys
Class 3The Value-Based ConversationDiscoveryWinning the Stage
  • You want to hire people who come from places with good personal PG
  • Save the Data: Simulation to put reps in the shoes of a customer going through a ransomware attack. People do a ‘table read’ of a ‘screenplay’ at their tables.
  • PG
    • Go into accounts with a compelling point-of-view. “I think you should be talking to me because ___.”
    • Don’t get stuck in research. Find one nugget and go.
    • Prep senior leaders and partners so they can reach out on your behalf
    • Research
      • How they make money
      • Who they compete with
      • What their challenges are
      • Product news
      • How they are organized
      • Executives / key people (news)
      • Challenges facing the industry; industry trends
      • What customer can I relate it to? A common challenge is even more important than company similarity.
  • Discovery
    • What are their challenges?
    • What are they doing today to address those challenges?
  • The Value Based Conversation
    • What problems do we solve?
    • How specifically do we solve them?
    • How do we solve them differently & better than anyone else?
    • Where have we done it before?
  • Building & Using the 3 Whys
    • Why do they have to buy? (not simply ‘Why buy (anything)?’
    • Why do they have to buy from us?
    • Why do they have to buy from us now?
  • Winning the Stage
    • Forget about winning the process, it is winning each stage.
    • Uses MEDDPICC.
    • Stage 1:
      • To create a Stage 1 qualified opp, there must be a mutually identified pain attached to a problem worth solving with someone who has influence that is willing to solve it and a calendared next step,
      • Inside Stage 1, we identify the key influencers, esp. multiple champions. Go wide and high.
      • Am I quantifying the pain?
      • Multiple people must validate the champion (ex: AE, first line manager, sales engineer)
    • Stage 2:
      • Put together a plan with the champion outlining what we need to do to win the deal
      • What is the financial side?
      • To exit Stage 2, you need to validate your close plan and general financial impact with the economic buyer
  • Sales leader training focuses on recruiting and coaching.
  • We don’t sell software; we teach champions how to sell the software. – Kaplan paraphrasing Brian McCarthy
  • The real champion will not emerge if you cannot quantify the pain. – McMahon
  • Rotate people in-out of sales enablement. They teach the classes but also get attached to deals to support (newer) reps. When you rotate them out, put them in bigger jobs. Ex: AE to enablement to first line management.

Moving into the CRO role with Kelly Connery – Nov 2023

  • As a CRO, you need to be in some ways a CIO because there are so many great technologies out there… You have to be good at leading cross-functionally whether your own Marketing and retention or just sales.

Scaling Sales at a Startup with Chris Reisig – Nov 2023

  • As an early stage CRO, you are a sales professional and a product manager at the same time.
  • If you cannot find pain at your customer that is acute in your customer, you have to keep looking. (5:16)
  • It is one thing if you and the founder can go out and do 10 deals, but unless you can teach other people to take a deal from first presentation to PO then you don’t have a repeatable business. If a founder can turn to me and say “Hey, the last 5 deals we did… I only came in to shake hands at the end,” then you there is something there. (7:19)

Selling the Vision with Devdutt Yellurkar – Nov 2023

  • You have to earn the right to be asked for help. You do this by listening, by not judging, and by only helping when you are qualified to do so. When you are not qualified, find someone else who is.
  • Founder CEOs will relentlessly pursue their vision. Non-founder CEOs will change the vision when they hit a wall.
  • User buyers have gained tremendous power in the software decision making process.

Breaking Down the Traits of a Champion with Anna Gary – Nov 2023

  • Start opportunity reviews with an org chart that shows both authority and influence.
  • To find a champion, look for people who are tasked with leading change.
  • There are both business champions and technical champions.
  • The biggest difference between a coach and a champion is that the latter has the willingness and ability to access the economic buyer. – John McMahon
  • Coaches tend to ask questions around technology fit; champions tend to ask questions around business impact.

Focus on the Fundamentals with Paul Ohls – Nov 2023

  • It is all about the quality of the people that you bring into your organization. Give hiring managers a set of interview questions to test for key attributes including (ICCE):
    • Intelligence: Listen for the qualify of questions people ask you about your business and the value of your products.
    • Character/Drive: Walk me through a time when you were tempted to throw in the towel but persevered – personal or professional.
    • Coachability: Go through every job a person had and ask them what they learned a long the way. What did you learn there and why did you leave?
    • Experience
  • It is a red flag during an interview process when people don’t take ownership for failure. They blame a bad boss, a bad product, etc.
  • If you work in a location geographically remote from headquarters, esp. in a different country, selling may not be as ‘different here’ as you think.
  • No matter what situation you come into as a new leader, there are going to be pockets of success. Dive in to understand the approaches of the people who have been successful in those functions.
  • Optimize your sales process by asking customers why they bought. Go deep – why did they take the first meeting? The second meeting?
  • As a new sales leader, show up with a playbook written in pencil rather than in permanent marker. Update it by diving into what has worked for that company in that market for that product set at that price point with that buyer persona.
  • Adjust probabilities by source (ex: AE self-sourced; channel; inbound; etc.)
  • Sales leaders must block out time every week to reach out to great candidates
  • Never take shortcuts when it comes to recruiting – John McMahon
  • The economic buyer (EB) in most organizations right now is the CFO.
  • Track critical conversion rates such as advancing from 1st new business meetings to 2nd technical deep dive discussions. This should drive your enablement focus.
  • Track pipeline generation in the trailing 90 days at the company, team, and AE level.
  • Productivity per ramped rep is the ultimate metric.

Key Points in Snowflake’s Growth with CRO Chris Degnan – Oct. 2023

(This episode is an excerpt/highlight of a prior full episode.)

  • If you build a business just on the large enterprise, then you are screwed. They will surprise you on the upside one quarter and on the downside the next.

Reducing Customer Churn with Pawan Deshpande – Oct 2023

  • Things CSMs say when there is a culture of futility:
    • ‘We reach out to the customer 3x and they never responded.’
    • ‘Sales oversold the product.’
    • ‘The product is flaky.’
  • Merge AEs and CSMs into pods so that CSMs are involved in active deals.
  • Have Product and CS train and certify AEs on how the product works.
  • Types of customer support/success:
    • Support: Addresses an acute point issue
    • Onboarding: Optimize for adoption
    • Business Reviews: Periodic, proactive look at the whole health of the account
    • Critical Care: Monitor the account for signs that something may be off and proactively engage. Examples:
      • low utilization – no usage in last 14 days
      • unpaid bills
      • broken 3rd party integrations
      • low NPS or CSAT
      • extremely negative support tickets
      • power user or admin changes
      • Acquisition of company
      • Champion departure
      • Major management change
  • During onboarding, strive to identify multiple champions so you can react more effectively if/when your primary champion leaves.

What the Best Sales Leaders Do with Brian McCarthy – July 2023

  • To love someone is to will the good in another. For a person to listen to you, they need to believe that you care about them.
  • Listen for text and sub-text with your eyes and your ears.
  • There is no decision that I make that I cannot unmake – I’d rather execute and course-correct as needed. Thoughtful speed has value.
  • People really start to learn when you involve them in role-plays and whiteboarding. – McMahon
  • The job of a 2nd line manager is to develop leaders.
  • Our 1:1s focus on early-stage pipeline – reviewing pipeline generation (PG) activity and preparing for 1st meetings.
  • Put enablement people in the field to directly coach and support reps and leaders.
  • Hire your way out of your job.
  • Your job is not to sell software; it is to focus on winning the stage. You do that by enabling champions to sell for you when you are not in the room. Champions sell software.
  • Exit criteria for Stage 2:
    (We win 83% of deals that exit Stage 2)
    • Access to the EB
    • Validated & tested the champion
    • 3 Whys rooted in quantifiable value
    • Influenced the required capabilities and validated them with the EB
  • Align critical capabilities to specific, quantified customer pain. – McMahon
  • Rep employee retention is a major driver of overall sales productivity. (Recruiting speed too.)
  • Adjust win rates by stage based on historical data by:
    • week in quarter
    • days in stage
  • Closely monitor days in stage for opps that advance; look at each step in each stage to address drift
  • Separate forecast category (commit, best case, pipeline) from stage

Coaches vs. Champions with Anne Gary – June 2023

  • A champion is someone with power & influence in the organization. They take action on your behalf. [JM]
  • Power is access to an economic buyer who has discretionary control over the budget [JM].
  • People with influence have experience in the organization as ‘change agents’
  • In your deals, identify & develop both business champions and technical champions. Business champions focus on outcomes and they rely on technical champions to evaluate the solution. [JM]
  • Coaches are not a waste of time but they are not sufficient to win a deal. Coaches look through the eyes of product fit and technology. Coaches don’t take action on your behalf.
  • You will get relegated down to the person you sound like. [JM]
  • Is your champion stronger than the competition’s champion?

All You Need to Know About Good Leadership with Jeremy Duggan – May 26, 2022

  • Three Rs – recruiting, retention, and revenue/results
  • Recruiting
    • Knowing what an A-players looks like
      • Intelligence
      • Character – resilience, determination, work-ethic, loyalty, honor
      • Coachable
      • Experience (really a nice to have)
    • Getting great people
      • As a hiring manager, working for an appealing company to begin with
      • Getting people inspired by the job they are doing, the people around them, their leaders
      • Showing people they will be developed (which required a track record)
  • Retention
    • Delivering on developing people
    • Do everything excellently
  • Revenue/Results
    • 5% of success is the ideas; 95% is the execution
    • Inspection with the purpose of developing people is not micro-management; it is a mechanism for improvement.
  • One of BladeLogic’s 4 compelling differentiators was its configuration object dictionary.
  • Leadership requires credibility (track record of high performance) and empathy
  • Leaders need to be aware of how others perceive them – McMahon
  • People referenced:
    • Tom Levey
    • Marty Carty
    • Paul Cant
    • Mark Musselman
  • There is a genius in simplicity; you can’t do something with 17 data tabs.
  • ‘Paying attention to leading indicators is what makes you the best in the world.’
  • One of PTC’s compelling differentiators appears to have been bi-directional associativity
  • Value pyramid (developed by Jeremy Duggan) – research & preparation for an EB meeting: (This differentiates you from other salespeople who just show up and pitch their product)
    • External influences on a prospect
    • The prospect’s strategic responses
    • How we can help (but only in the areas we address)

Execute a Winning Strategy with Chuck Bamford – May 2023

  • Half of strategy is not frustrating your customers relative to what they can get with competitors; these elements are table stakes. The other half is coming up with 2-3 things that are true competitive advantages then aligning the whole organization around .
  • Customers compare you to competitors every day.
  • Continue to analyze two types of competitors: (5 competitors is sufficient)
    • Those you bump into in every deal
    • Those on the fringe who are doing innovative things
  • Company strategy must be converted to KPIs. Those KPIs must then be converted to the activities frontline workers do every day.
  • If you ask me to do something that does not help my sales people sell more, then I will say no… it will not be one of my priorities. [JM]
  • During challenging times, double down on your strategy.
  • John McMahon’s ICP process
    • start with your competitive diffentiators
    • ask, ‘Which pain points do those differentiators solve?’
    • What use cases are those pain points in?
    • Who owns those use cases?
    • How are those people measured in their job?
    • What is a reasonable value for helping them achieve those measures?
    • Point your salespeople at those companies and those personas who place the maximum value on the solved pain.
  • New features must become a new differentiator or enhance an existing one. [JM]
  • A startup can only focus on 3-4 use cases. [JM]
  • A company does not have a healthy culture if it does not invest in training is employees and ensure its people can achieve their target earnings. [JM]
  • A differentiator must (1) have clear, provable value to the customer and (2) be something your competitor truly does not have. It is not sufficient to just have a feature that your competitor does not. [JK]
  • Do win reviews: [JK]
    • Why did you buy from us?
    • Where are not as good as we think we are?
    • Where are we better than we realize?
    • What seller would have bought from if they had a better product? Always be recruiting.
  • Sellers must influence your differentiators into the buyer’s Decision Criteria. That only happens if they acknowledge the differentiator creates value by solving a pain point. [JM & JK]

Selling to the CFO – Apr. 2023

  • Murray Demo, 6 time CFO
    • I would only meet with a sales person at the request of one of my peer executives and only once the deal nearly final. I expect my peer to sell to me.
    • Purchases that reach my desk are large enough to cut across my company. I need to know the teams affected are committed to business process change. I spend more time around that than squeezing the last dollar out of the price.
  • Jim Kelliher, Drift CFO
    • Each quarter, we look at:
      • Top line growth in new business & expansion
      • Productivity of new reps and ramped reps
      • GDR & NDR
      • Employee attrition and ramped quota capacity
      • Cash burn
    • Forecasts need to be sensitive to rep ramp time
    • Missing your forecast is a sign you don’t truly know you are accounts. – John McMahon

Healthy Growth and Taking Risks with [CFO] Hope Cochran – Mar 2022

  • “[As a CFO,] I do not respond sell to cost justifications. I respond well to solutions… [that] make sure my systems and processes keep up with our growth trajectory.”

Get to Know Your Hosts – Feb 2022

(no highlights for this episode)

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