- Sales Management: Key Responsibilities that Will Make or Break Success – Oct 24, 2024
- Optimizing a Customer Success Team with Sasha Anderson – Sep 26, 2024
- Building a Strong Sales Team: Recruitment, Interview, and Onboarding Best Practices with Marcy Stoudt – July 11, 2024
- The Impact of AI on Sales with James Underhill – April 11, 2024
- The Path to Sales Leadership: Lessons Learned at Each Management Level with Carl Cross – Jan 18, 2024
- Three Traits of a Successful Revenue Partnership with Alan Chhabra – Jan 14, 2024
- The Startup CEO with Jeremy Burton – Jan 11, 2024
- Loyalty and Culture with Hollie Castro – Jan 7, 2024
- Business Value Assessments: Looking at Opportunities through a Value Lens with Doug May – Jan 4, 2024
- Driving Sales Productivity with JP Bolen – Dec 2023
- Moving into the CRO role with Kelly Connery – Nov 2023
- Scaling Sales at a Startup with Chris Reisig – Nov 2023
- Selling the Vision with Devdutt Yellurkar – Nov 2023
- Breaking Down the Traits of a Champion with Anna Gary – Nov 2023
- Focus on the Fundamentals with Paul Ohls – Nov 2023
- Key Points in Snowflake's Growth with CRO Chris Degnan – Oct. 2023
- Reducing Customer Churn with Pawan Deshpande – Oct 2023
- What the Best Sales Leaders Do with Brian McCarthy – July 2023
- Coaches vs. Champions with Anne Gary – June 2023
- Execute a Winning Strategy with Chuck Bamford – May 2023
- Selling to the CFO – Apr. 2023
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
- Prospecting to consistently build pipeline with a clear rhythm:
- 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
- Recruiting, developing, training, and retaining a team of 5-7 A-player reps
- 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
- Recruiting, developing, and training a team of A-player 1st line managers
- 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
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
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 A | Track B | Track C | |
Class 1 | Save the Data | New Business Meeting Prep | Champions |
Class 2 | Pipeline Generation (PG) | Messaging | Building & Using the 3 Whys |
Class 3 | The Value-Based Conversation | Discovery | Winning 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?
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
- Each quarter, we look at: