In this comprehensive discussion, Kyle delves into his extensive career journey, sharing invaluable insights and strategies that have fueled his success in the fast-paced world of sales.

From frontline management to effective sales leadership, innovative sales tactics, and the evolving role of AI in sales, Kyle offers a treasure trove of knowledge and experience for anyone looking to excel in this dynamic field.

Also, don't forget to check out our previous blog, where we put together a list of 20 must-follow GTM experts for SDRs & AEs.

Can you share a bit about yourself and your career journey so far?

Thanks for having me. Currently, I run revenue at Owner.com. We serve independent restaurants across the US, similar to a combination of Shopify and HubSpot for small restaurants.

We power everything online so restaurants can interact directly with their customers, enabling them to get orders online instead of through third-party services, grow their business, and make more money.

I've been in sales my entire career, starting right out of university. I began making cold calls and gradually progressed to managing teams, eventually overseeing multiple teams.

This led me into the SaaS world. I ran gold BDR for Vision Critical, a Canadian company, then managed sales at a startup called League, taking their lead from zero to twenty-five million in three years in the Healthtech sector.

After that, I spent three years at Shopify in various roles, including running the Canadian market, a two hundred and fifty million dollar business unit across all segments and products.

I thoroughly enjoyed my time at Shopify, appreciating the mission and the people. I then returned to the startup arena, joining owner.com when it was at around three million in ARR.

Eighteen months later, we've reached about fifteen million. In my current role, I oversee sales, revenue operations, enablement, and our launch function. That summarizes my career journey.

What tips or frameworks would you share for sellers transitioning into frontline managers? 

I have started documenting a framework for my team, addressing the transition from being a rep to a managerial role, focusing on what to do, where to spend time, and other sales management best practices. The framework includes several pillars:

Sell: Maintain the ability to sell or execute the craft. Assist your team in closing deals or launching customers, demonstrating what good looks like, keeping your skills sharp, and ensuring targets are met.

Coach: Spend at least an hour with each team member, coaching them to improve. This could involve comparative call listens, mock calls, or dissecting parts of the outreach process.

Hire: Be able to source, scorecard, select, and secure the right talent. This involves creating a structured hiring process.

Operate: Manage day-to-day operations. This includes setting weekly operating rhythms, keeping the team on task, managing forecasts, and maintaining meeting, one-on-one, and reporting cadences. Ensure the business runs smoothly.

Build: In startups, understand the revenue system and make incremental improvements. Identify data-driven opportunities for improvement and update business processes or develop new strategies for revenue acquisition.

Inspire: Engage and inspire your team daily. Help them pursue mastery, find purpose in their work, and feel a sense of autonomy and empowerment. Balance micro-management and micro-coaching, providing autonomy, mastery, and purpose to foster inspiration and engagement.

In summary, effective sales leadership means being able to sell, hire, coach, build, operate, and inspire.

Which pillar do you find most overlooked and why?

The 'operate' pillar is most likely overlooked because it is not very fun and is quite operational, which does not come naturally to many salespeople and sales leaders. We entered this business to chase deals and engage in novel, interesting activities daily.

As a manager, you need to focus on defined systems. For example, on Friday afternoons, I write my weekly report, review Salesforce dashboards, spot-check information, and ensure my forecast is well-organized. This includes running team meetings and setting formats for one-on-ones.

This work can be a grind. I enjoy the problem-solving aspect, which is why I like doing what I do. However, it might not be exciting for everyone and it's different from what is often taught. Although more content on this topic is now available, such as Kevin Dorsey's course on being a good operator, it's still probably not addressed adequately in many places.

Can you elaborate on best practices or frameworks for hiring and coaching?

For hiring, I use the 'source scorecard select secure' framework from the book 'Who.' Before posting a role, we create a scorecard outlining the competencies and traits required for the role and how to measure them. This is part of our hiring toolkit.

Our sourcing process is akin to outbound sales, involving candidate sourcing. A significant part of my sourcing involves writing content on LinkedIn to build an audience, generating an inbound funnel over time.

Regarding interview structure, we have three interviews in our process, each asking the same questions in the same order. This structure reduces cognitive bias significantly, allowing for a fair comparison among candidates and reducing general bias in the hiring process. It also improves the candidate experience, which is crucial.

A structured, rigorous interview process makes candidates feel valued, regardless of the outcome. This attention to detail in the candidate experience can also make them more likely to accept an offer and speak positively of the brand, even if they are not hired. Documenting and structuring this process carefully is critically important for both the company and the candidates.

Can you share an innovative practice or unique sales strategy that had a significant impact?

One of the most important strategies we implemented at Owner is investing significantly in data quality. This realization came when analyzing my team's activities at Vision Critical. I audited the quality of leads based on several criteria and found that about forty percent of the activities were wasted due to incorrect contacts or low-quality leads. This is a common issue when Business Development Representatives (BDRs) do their own lead research, leading to varying quality.

To address this, we've developed a sophisticated system involving database enrichment, web scraping, lead verification, and AI integration, which delivers high-quality leads to our team.

This approach has increased our team's productivity by about two and a half times on a close win basis. Previously, BDRs were spending about fifty percent of their time on non-revenue generating activities, which was inefficient.

By investing in high-quality data – which involves more than just purchasing leads from databases but includes several levels of grooming and data preparation – we've significantly improved our efficiency. We even use overseas contractors for manual phone verification of leads we cannot digitally verify, which costs us a buck per lead but is more efficient than having BDRs waste time on bad leads.

This focus on quality data makes the BDR role more enjoyable and engaging. It allows team members to spend more time calling good leads, which accelerates their growth and makes them feel like they're winning.

It's crucial for building a culture where people feel they're making progress and contributing to the business, rather than being bogged down by administrative tasks in tools like Salesforce.

How do you see the evolution of AI in sales?

The current application of AI, such as writing email content at scale, is one of the lower value applications. The incremental benefits are small, and the content often sounds like it was generated by a robot.

However, we use AI more significantly internally. One major use case involves a tool called Momentum, which integrates with Salesforce and Slack. When a demo call is completed, the AI scans the call and prepopulates fields in Salesforce, allowing reps to quickly update data.

This process accelerates the acquisition of data from unstructured environments, like call transcripts, and structures it into Salesforce. This enriches our sales database, making it more useful for reps. Over time, as AI in Salesforce improves, it will provide insights into our database, like the likelihood of winning a deal or identifying warning signs.

Another tool we use is called Replays, which uses AI to score sales calls at scale. Initially skeptical, I was impressed by the results from a consulting engagement with Replays. We used it for a ten-week training program, which increased our win rates from thirty-eight percent to fifty-three percent in that period.

These internal-facing uses of AI, such as enriching databases and scoring sales calls, are more interesting and impactful compared to using AI for mass messaging in marketing.

‍

As we conclude this enlightening conversation with Kyle, it's clear that his journey and expertise in sales and management offer a wealth of knowledge for anyone in the field.

His practical sales managemer tips and innovative strategic approaches, especially in utilizing data and AI, are not just inspiring but also actionable for sales teams aiming to optimize their operations and workflows.