The Sales Playbook to Scale from $2M to $40M

"I wish I had been more insistent about hiring a head of applied AI... I want somebody dedicated to go absolutely all out on it."

• Consider hiring specialized AI roles.
• Integrate AI tools into sales processes proactively.
• Early AI investment leads to competitive benefits.

"It's easy to feel good about helping like a restaurant down the street... that is a special part of owner's DNA... this collective is pretty special."

• Align team work with a meaningful mission.
• Foster a culture valuing collective achievement.
• Attract talent committed to your vision.

"We've had more success hiring people in like a 2 to 4 year experience range... we're highly opinionated about how we want things done... more senior reps come in and like, 'I know how to do this.'"

• Less experienced reps may adopt methodologies better.
• Experienced reps might resist new systems.
• Invest in training reps who align with your approach.

"The style of selling that I teach is radically transparent selling... we lead with both the strengths and weaknesses of the product... the wrong customers opt out immediately."

• Embrace transparency to build credibility.
• Qualify leads by highlighting who it's not for.
• Focus on right customers to reduce sales cycles.

"This is why it is so important to have a multi-channel strategy... as certain channels hit saturation... you've got other places to go."

• Don't rely on a single sales channel; diversify.
• Experiment with different channels for growth.
• Adjust focus based on performance changes.

"We centrally manage every lead... we get 95% of our leads mobile enriched... our call to decision maker connect... went from 3% to 13-16%."

• Use data enrichment to improve contact rates.
• Invest in AI tools to automate sales processes.
• Centralize lead management to let reps focus on selling.

"We've built and rebuilt... this onboarding program... week one is mostly remote and asynchronous... week two, everybody comes in person... doing much more practical application."

• Create a comprehensive onboarding combining remote learning and in-person training.
• Use call recordings and simulations to teach methodologies.
• Invest early in enablement to support scaling.

"It's so tempting to just try to get a body there... you have to hold a really high bar... The pain of getting it wrong is so significant."

• Resist filling sales roles with unqualified candidates.
• Maintain high standards to avoid long-term setbacks.
• Acknowledge that early hires impact company trajectory.

"I use Teresa Torres' Opportunity Solution Tree... It's a way to map from symptom to root cause... It forces you to more deeply ideate and solve problems more foundationally."

• Implement the Opportunity Solution Tree to diagnose sales challenges.
• Focus on root causes rather than symptoms in sales.
• Use product tools to enhance sales team performance.

"You can't be taken seriously at Shopify without being well versed in the language of product... being proficient in product knowledge made me a better sales leader."

• Sales leaders should build strong product expertise.
• Cross-functional fluency leads to better strategies.
• Understanding the product aids in crafting compelling pitches.