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Secrets to Sales Mastery: Proven Strategies

May 19, 2024

4 minutes

Adam is jetting off to France and Spain to visit a client, but let's be honest, it's mostly for fun! Don't worry, though; we've gathered some valuable insights to help boost your sales growth this week. Get ready to level up your sales game with tips from my time at Adobe, discover how aligning sales and customer success can boost your NRR, and dive into an awesome workshop from Winning by Design.

On Deck

  • Aligning Sales and Customer Success to Focus on NRR
  • Lessons Learned as a Fractional GTM Leader
  • Content We Can't Get Enough Of


During my time at Adobe, I was part of the journey to create their world-class Adobe Sales Academy. After hiring and training over 300 sellers in the program, I learned a few key valuable lessons that can be applied to build a world-class program at any company, regardless of its stage, whether it is a start-up or an enterprise. Let’s dive in!

1. Define the Attributes of what Awesome Looks Like

At Adobe, we have discovered that the best sales professionals possess certain key traits, which have since proven to be consistent regardless of where I have worked:

  • Emotional Intelligence: The ability to uncover their buyer's business and technical problems which spending more time listening than talking. They practice self-control to manage emotions, both personal and those of others.
  • Self-motivation: A strong internal drive to achieve goals. A desire to win the right way, no matter what.
  • Customer Focus: Prioritize customer needs and experience over their own self-interests. Never cut corners on a deal.
  • Technical Proficiency: Navigate and leverage the technology ecosystem effectively.
  • Grit: Resilience and perseverance. Stay laser-focused after a hard day, week, or month, and never complain about fairness.
  • Gratitude: They appreciate every growth opportunity they're given and embrace the challenge.
  • Humility/Coachability: They recognize the value of teamwork and continuous learning, always open to feedback.

Forget the fancy degrees. What really matters is if they can deliver. So, hire for these traits, and you’ll build a team of sales superheroes based on meritocracy. Create your own list of 5-7 non-negotiable traits and use it to guide your hiring process. Trust me, this is your foundation.

2. Implement Continuous Training and Development

Sales enablement isn’t a “set it and forget it” deal. Commit to investing in a kick-ass coaching culture. Here’s how to keep the learning train chugging along:

  • Onboarding and Reboarding: Think of onboarding like the first day of school, but with more Redbull. Document your process and give new hires proper time to learn, certify, and master mission-critical curriculum. Regularly refresh your team’s knowledge with reboarding sessions.
  • Diverse Training Methods: Mix things up with online courses, in-person workshops, role-playing exercises, and certifications. NOBODY wants to learn 100% from asynchronous training videos. There is no replacement for in-person training and coaching. Variety is the spice of learning!
  • Coaching and Mentoring: Create a peer mentor program where experienced sellers and leaders mentor new hires. It’s like having a sales Yoda by your side.

3. Focus on Leading Indicators, Not Just Results

Define KPIs based on leading indicators, use data to pinpoint areas for improvement, and create individual coaching plans for each rep. Remember, your goal is to coach excellence, not to play whack-a-mole with underperformers. Tracking lagging indicators is like looking in the rearview mirror. Instead, focus on what’s ahead:

  • Activity Metrics: Keep tabs on discovery calls, qualification calls, and opportunities created. Early course corrections save the day.
  • Behavioral Metrics: Pay attention to the quality of interactions and adherence to best practices.
  • Coachability: Measure how well your reps take and apply feedback. Adaptability is key!

4. Leverage Technology to Enhance Performance

Repeat after me: Activities and behaviors matter just as much as results. Implement a sales tech stack that measures leading indicators. Give your team a real-time dashboard that tracks performance so they can course-correct. The right tech stack can make or break your sales enablement efforts. Here’s what you need:

  • CRM Systems: Your central hub for customer data.
  • Revenue Intelligences Platforms: Insights galore! Track performance and spot areas for improvement.
  • Content Management Systems: Measure buyer engagement to focus efforts in the right place at the right time.
  • AI and Conversation Intelligence Tools: Use AI to analyze sales calls, track engagement, and provide personalized coaching.

5. Create a Culture of High-Value Behaviors

Encourage your sales team to focus on behaviors that deliver consistent results:

  • Preparation and Research: Make account prep as essential as morning coffee.
  • Empathy and Effective Communication: Teach reps to use empathetic tonality and ask insightful questions.
  • Networking and Social Selling: Use personal networks and social platforms to generate leads and build rapport.
  • Time Management: Teach sellers how to manage and protect their time to focus on high value sales activities.

6. Scale Successful Practices Across the Organization

Prioritize results over stale processes and make changes to standardized processes when needed. When you find something that works, shout it from the rooftops and scale it across your team:

  • Standardized Processes: Develop clear, repeatable processes for onboarding, training, and performance evaluation.
  • Knowledge Sharing: Share best practices and success stories through wikis, internal forums, slack, and regular team meetings.
  • Continuous Feedback: Create a culture where feedback flows freely and everyone is on a journey of continuous improvement.


These six practical steps for creating a sales enablement program will help your startup build a strong reputation that attracts and retains top talent. But don't just take my word for it – roll up your sleeves and get to work! Remember, investing in your sales team's growth is like compound interest: The sooner you start, the bigger the payoff. By focusing on the right traits, implementing continuous training, tracking leading indicators, leveraging technology, and fostering a culture of high-value behaviors, you can set your sales team on a path to greatness. Start small, iterate, and scale your efforts.

If you have questions, thoughts, or tweaks, I want to hear them!

Aligning Sales and Customer Success to Focus on NRR

Recently, I had the pleasure of presenting at the Utah Customer Success Meetup hosted by David Blake, CEO of ClientSuccess, in front of a highly engaged audience of around 80 people. The session received overwhelming feedback, emphasizing the importance of aligning sales and customer success teams to drive Net Revenue Retention (NRR). Here are the key takeaways from that presentation, distilled into actionable insights for your startup.

1. The Importance of NRR

Net Revenue Retention (NRR) is a critical metric for SaaS startups. It reflects the revenue retained from existing customers, including expansions, contractions, and churn. A high NRR indicates strong customer satisfaction and loyalty, which are essential for sustainable growth. By focusing on NRR, you can ensure that your growth is not only driven by new customer acquisition but also by maximizing the value of your existing customer base.

2. Creating an Ideal Customer Profile (ICP)

Define your ICP based on revenue potential, product usage, and customer behavior data. This helps identify customers who are likely to expand their relationship with your company. Use the information you know about your customers to refine the ideal tech stack configurations that indicate a need to expand.

Action Item: Develop detailed ICPs to guide both sales and customer success efforts.

3. Collaborative GTM Strategy

Develop a Go-to-Market (GTM) strategy that involves both sales and customer success teams. This includes joint planning sessions and shared goals to ensure cohesive efforts. Align your products with customer cohorts and their revenue expectations.

Action Item: Schedule regular strategy meetings between sales and customer success teams to align on goals and tactics.

4. Customer Journey Mapping

Map out the entire customer journey, from onboarding to renewal and expansion. Identify key touchpoints where collaboration between sales and customer success can enhance the customer experience. Use the 5 D’s of Customer Value (Delays, Disillusionment, Dilution, Disconnected, Disengagement) to identify and address potential issues in the customer journey.

Action Item: Create a detailed customer journey map highlighting areas for sales and customer success collaboration.

5. Data-Driven Decision Making

Utilize data to track customer health and identify opportunities for upsell and cross-sell. Implement dashboards that provide real-time insights into customer behavior and engagement. Data-driven early warning systems can help proactively address customer issues before they lead to churn.

Action Item: Invest in analytics tools that integrate with your CRM to provide actionable insights for both teams.

6. Regular QBRs and Check-Ins

Conduct quarterly business reviews (QBRs) and regular check-ins with key accounts. These meetings should involve both sales and customer success to discuss performance, gather feedback, and identify growth opportunities. Outcome-driven QBRs can highlight customer ROI and ensure that your team is focused on delivering value.

Action Item: Establish a schedule for QBRs and ensure that both sales and customer success teams are actively involved.

7. Fostering a Culture of Collaboration

Foster a culture where sales and customer success teams work together towards common goals. This involves cross-functional training, shared incentives, and open communication channels. Emphasize the importance of both digital and human touchpoints in post-sales processes to ensure a seamless customer experience.

Shared Incentives: Align compensation and incentives to encourage collaboration. For example, link part of the customer success commission to NRR targets.

Cross-Functional Training: Provide training sessions that cover both sales and customer success skills, ensuring team members understand each other’s roles and responsibilities.


Aligning sales and customer success teams is a strategic move that can significantly enhance your startup’s NRR. By creating a cohesive customer journey, leveraging data for decision-making, and fostering a collaborative culture, you can drive sustained growth and build stronger, more profitable customer relationships.

Lessons Learned as a Fractional GTM Leader

In this new section, we aim to bring you real-life lessons each week, either from us or from one of the founders we work with.

All names have been changed to protect the identities of others...

Recently, I had an intriguing conversation with a startup founder named Jennifer, who sought my advice on a critical decision. Jennifer wanted feedback on two existing sellers on her team and whether they should be kept on as the company shifted its strategy from SMB to enterprise. Here's how the conversation unfolded and the impactful lessons we can draw from it.

Jennifer: "I've got these two sales reps who have both been with us for the past six years. With our new shift to targeting enterprise clients, I'm not sure if they can make the cut. What has been your take since working with them for the past several weeks?"

Me: "It's an interesting challenge, for sure. Let's consider a couple of things for a moment. How would you describe their approach to learning new skills?"

Jennifer: "Honestly, they don't seem very eager to learn. They’ve been doing things the same way for years, and while they don't necessarily resist new training initiatives, they don't really apply themselves to adapting to the changes."

Me: "Got it. And what about their sense of urgency? Do they consistently hit their targets and push to close deals?"

Jennifer: "Not really. Neither of them hit their quota last year, and neither has closed any deals in the past five months. It didn't used to be this way, but there hasn't been any real drive in almost a year. They seem to coast along, just doing the minimum required."

Me: "Hmm, that’s telling, isn't it? How would you characterize their reaction to the zero-accountability culture you’ve mentioned in the past?"

Jennifer: "They’ve become too comfortable. They don't feel the pressure to improve or perform beyond what's necessary."

Me: "And considering our new Enterprise GTM strategy, do you believe they have the skills to handle the complexities and demands of enterprise-level sales?"

Jennifer: "I'm skeptical. They’ve only ever dealt with SMB clients, and I'm not convinced they have the chops for enterprise sales."

Me: "Sounds like we've painted a pretty clear picture. Let me ask you this: If you had the chance to rebuild your team from scratch with enterprise sales in mind, would these two be part of that new team?"

Jennifer: "Probably not. They don’t seem like a good fit for where we're headed."

Me: "So, what steps do you think are necessary to align your sales team with the new strategic goals?"

Through this Socratic dialogue, Jennifer began to see the misalignment between the current sales reps and the company's new strategic direction. Here's the crux of the lesson:

  1. Desire to Learn: A growth-oriented mindset is crucial for any sales team, especially when shifting to more complex markets. If reps aren't eager to learn and adapt, they're unlikely to succeed in a new, more demanding environment.
  2. Sense of Urgency: Urgency drives results. Reps who lack this will struggle to keep up with the fast-paced demands of enterprise sales, where closing large deals quickly can make a significant impact.
  3. Accountability Culture: A culture without accountability breeds complacency. For a team to thrive, especially in competitive markets, there must be clear expectations and consequences.
  4. Willingness to Change: As startups pivot and evolve, the sales team must be agile and capable of scaling their skills to meet new challenges. Reps who can't adapt are a liability.

It's vital to continuously evaluate your team’s fit with the company’s direction. Don’t shy away from tough decisions that can propel your startup forward. Aligning your sales team with your strategic goals isn't just a nice to have; it's essential for sustainable growth.

Content We Can't Get Enough Of: Winning by Design's Revenue Architecture Workshop

If you're a startup founder or a head of sales looking to elevate your revenue architecture game, I've got some exciting news. Jacco van der Kooij and Dominique Levin from Winning by Design, renowned experts in sales and revenue architecture, just announced an incredible opportunity that you won't want to miss.

Their inaugural revenue architecture class is officially open for registration in Santa Cruz, California!

Why This Workshop Stands Out

  • Practical Learning: Centered around the Revenue Factory concept, the course offers hands-on experience and actionable insights that you can apply immediately.
  • Expert Instruction: Learn from Jacco and his team of seasoned experts who bring a wealth of knowledge and personalized guidance.
  • Beautiful Location: Enjoy the stunning surroundings of Santa Cruz, right by the beach.
  • Intimate Setting: With only 20-30 participants, this workshop offers personalized learning and valuable networking opportunities.

Why You Should Attend

This workshop is perfect for anyone looking to refine their revenue strategies. It’s a unique opportunity to gain cutting-edge insights and connect with like-minded professionals.

Don't Miss Out

Spaces are limited, so I highly recommend checking it out if you're looking to transform your revenue approach.

Register here: https://winningbydesign.com/revenue-architecture-summit-2024/


In our latest episode, Keith joins the Revenue Reimagined podcast to discuss his sales experience and career journey. Weightman believes that people work for people, not companies, which is why he has stayed at Bullhorn for over a decade. He credits his longevity to working with great leaders and having the right people, product, and environment to succeed. Weightman also emphasizes the importance of core values and mission in guiding a company’s actions and decisions. He shares his tips for combining sales, writing, and visualization to deliver impactful newsletters.

During the show, Keith explains:

  • the power of visualization and writing ✍
  • what a good leader can do for an organization 🏛
  • what a good set of core values can do for a company 💝

Any founder, entrepreneur, or business leader can steal Keith's lessons in this episode and use them for their own success.

Check out the show here.

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