Lessons from Kyle Asay, VP Global Sales at LaunchDarkly

On Sales Strategy and Execution

On the purpose of discovery: "Discovery is a balance of better understanding true customer problems while educating them enough that they are confident that you can solve them to encourage them to continue the conversation." [1]
On effective demos: "People usually buy things that they know how they would use and how they'd benefit. People don't buy things that look cool but they have no idea how would fit into their environment." [2]
On avoiding generic demos: "Eliminate the words '30,000-foot view' and 'high-level overview' from your demonstration vocabulary." [3]
On personalizing demos: "I had to design my product demos to match as closely as possible to how the customer would actually use our solution." [2]
On entering discovery with a hypothesis: "Always entering discovery with a point of view and a value hypothesis... I came prepared to get deep into how we could likely help them." [2]
On the ideal discovery checklist: A successful discovery means you leave the call knowing the one or two problems important enough for the customer to actually solve. [1]
On understanding the customer's current state: A key piece of successful discovery is understanding what customers are currently doing to solve their problems; if it's nothing, you haven't found a big enough problem. [1]
On maintaining control of the deal: When a buyer says, "Let us think internally and get back to you," you have to maintain control by walking them through exactly what they likely would have to do next to get approval. [2]
On creating your own account scoring model: "I created my own account scoring model that ensured I worked with the accounts most likely to purchase... their job is not to dictate where you as an individual rep spend your time." [2]
On identifying budget potential: A good indicator for budget is if a company is hiring more engineers, which means they are likely building more applications and investing in solutions. [2]
On the power of customer stories: "The best way to sell that next step is giving them confidence that you've done this before you've helped somebody else similar to them solve a similar problem and that is where customer stories become your best friend." [1]
On the continuous nature of discovery: "You're never fully done with Discovery. I think a big mistake reps make is treating Discovery as a stage in the sales process and not an ongoing conversation." [1]
On balancing learning and educating: In a discovery call, you need to balance what you want to learn from the buyer with what they want to learn from you to drive a mutually beneficial conversation. [4]
On the importance of a value driver: A value driver is something that generally exists in an account with or without your company; it's important to them and should tie back to something you do very well.
On turning a feature-led product into a platform story: Learn how to tweak your initial pitch across different value drivers and then tie it to the product.

On Leadership and Team Management

On the most important trait for a leader: "The most important trait for a leader is to be an effective teacher."
On scaling as a leader: A big piece of scaling as a leader, from front-line to global, is effective delegation. [5]
On setting consistent goals: "I think a lot of leaders struggle with goal setting cuz they're always trying to pivot and find the next new thing to go after and it creates this ongoing skepticism within the org."
On rapid onboarding: "Reps that do really well long-term often start fast and so we focus a lot on how quickly we can get people to their first conversation." [5]
On onboarding focus: The three focus areas for rapid onboarding are: knowing your territory, understanding your personas, and knowing your stories. [5]
On getting rep buy-in: When implementing changes, also listen to what the team needs and make it happen as quickly as possible to build trust.
On the value of high-integrity people: "If you don't have the kind of high integrity, incredible people that I'm lucky to work with it all falls flat... a leader can't take credit for that."
On forecasting vs. development: "I would rather have a leader roll up an inaccurate forecast than drop the ball on accountability and development because if they drop the ball on the forecast, we'll be inaccurate for a short period... if they drop the ball on accountability and coaching, we're going to miss forecast for quarters to come."
On managing performance with key metrics: The three core metrics to manage performance are this quarter's revenue, this quarter's AE-sourced pipeline, and next quarter's pipeline coverage.
On the "Good Day Framework": "Give your reps multiple ways to get to a 'good day' — build a Good Day Framework that assigns points to both inputs and outcomes." [6]
On coaching: "Pick 1-3 competencies to coach a rep on max. Train your team, then establish a coaching rhythm to reinforce the training and a metric to track it." [6]
On hiring for traits vs. skills: "Traits suggest the potential for an AE to succeed in a role, and then skills determine how likely and quickly an AE will hit potential in a role with the company." [7]
On desirable traits in a candidate: The best AEs are coachable, have high IQ and EQ, possess an internal locus of control, and show a great career trajectory. [7]
On essential skills in a candidate: Look for pipeline generation ability, a good understanding of sales methodology, and technical acumen/industry experience. [7]
On the human element of management: "There's a very human emotional element to sales, and that connection is going to be essential to help people get through... if I didn't have a good manager helping me through that I wouldn't have made it." [4]

On Personal Development and Mindset

On overcoming struggles: "I need to either commit to this and go all in put all my effort in and accept the outcome, or I need to walk away from it and find something that I can commit to." [4]
On avoiding a victim mentality: Don't fall into a victim mentality of blaming your territory or inbound leads for a lack of success. [4]
On the "Effective Day Framework": "I've never managed a rep that missed quota when they consistently succeeded in applying my framework for an effective day." [8]
On measuring what matters: "Notice I don't measure calls made... I measure people talked to... making 60 calls and talking to no one is a successful day it's just a big waste of time." [8]
On continuous learning: "Reps can get really busy, but they forget how important it is to sharpen their saw." [8]
On choosing the right environment: "Your career is not often going to grow faster than your company is able to grow... you need to fix the environment first and foremost."
On mastering your craft: "If you haven't made changes in your leadership approach in the last 6 months you're already behind." [9]
On the internal locus of control: "They largely feel like their success or failure is up to them." [7]
On the importance of grit: "I want to know that you're in it to help us get through challenges not just run away to find an easier job as soon as it gets tough." [7]
On the path from failure to success: Kyle Asay went from hitting quota only once in his first two years as an AE to becoming the #1 AE out of over 200. [2]

On AI and the Future of Sales

On the role of AI in sales: "Use it to accelerate, but don't get overly dependent... learn to think, learn to process, learn to learn all the aspects of sales, and let AI accelerate you." [4]
On the limits of AI outreach: "The better it gets, the less effective it's going to be because the power of AI is becoming personalized, relevant, timely very, very quickly. But if I'm looking at my inbox and every single email is relevant, timely, and personalized, by default nothing is relevant, timely, or personalized." [4]
On AI augmenting, not replacing, sellers: "We don't think that AI can replace all sellers right now, but what it can do is supercharge the sales team." [4]
On the human element in an AI world: "The sellers that build part of the point of view with AI go the extra mile to have the conversations to go deeper, they are going to win with the efficiency, while doing that last mile that only humans can do for now." [4]
On the future of sales leadership with AI: AI will likely allow for larger spans of control for managers by taking on tasks like call scoring. [4]
On the widening gap due to technology: "The accelerator from technology is only going to widen that Gap... top performers, they're not looking for shortcuts they're looking for accelerants." [10]
On the ethical implementation of AI: The intent should be to make every individual in the company stronger, not just to drag every ounce of production from them until they burn out. [10]
On the resilience of the sales profession: "The phone was going to kill the salesperson, everything is going to... We're a very resilient people." [4]
On the importance of human connection: "If the end outcome is just AI being used to always the optimal scenario with no human conversations, maybe that's great for ROI and shareholder value but it isn't really a world that I want to play in or be a sales leader in." [4]
On the irreplaceability of certain human interactions: "I would like to see any AI get deal updates like I can, it's this mixture of passive aggressiveness and humor, it can't be replaced." [4]

Learn more:

Lessons from Kyle Asay, VP Global Sales at LaunchDarkly

On Sales Strategy and Execution

On Leadership and Team Management

On Personal Development and Mindset

On AI and the Future of Sales

Written by Antoine Buteau

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