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Sales masters

Taylor Corr’s leadership lessons from managing a 40+ member sales team

December 14, 2023

Arjun Krisna

In this edition, we're thrilled to share an exclusive interview with Taylor, a seasoned sales leader with over nine years of experience.

Taylor's journey from an account executive to a pivotal role overseeing frontline managers and leading the sales channel is not just inspiring but also filled with valuable lessons.

In this Q&A, Taylor sheds light on the skills that propelled their career, the significance of emotional intelligence in sales, the nuances of managing and developing sales teams, and much more.

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?

Of course. I have been in this field for nine and a half years, which feels like an eternity. I started as an account executive and was in that role for a few years as an individual contributor. Along the way, I had opportunities to learn sales management and transitioned into a sales manager role for two to three years.

I've been in my current role for about five years now, overseeing frontline managers and leading the sales channel.

What skills or experiences were most instrumental in your career progression?

A couple of things were important in my career progression. Firstly, mastering your core role is crucial, especially the role of an Account Executive (AE). This is vital because as a new manager, you will rely heavily on the skills you developed as an AE to support your team and learn about becoming an effective leader.

the Becoming strong in your role, overcoming challenges, and accumulating wins provide valuable experience for later stages of your career.

Secondly, building up emotional intelligence is essential. This involves becoming a great communicator and understanding how to balance your emotions. Being calm, collected, and confident helps in becoming a better leader. Focusing on these aspects of emotional intelligence has been instrumental in my growth into my current role.

Can you share an example of an exercise you did for emotional development?

One exercise I focused on, especially as a manager, is self-regulation. This involves creating more time between your initial gut reaction and your actual response. For instance, when someone says something that might seem frustrating or annoying, the goal is to react in a more measured way.

This doesn't happen overnight. I maintain a manager journal, where at the end of most days, I reflect on my workday. I consider situations where my reactions were effective and where they were not, reinforcing learnings and habits.

Reflecting on how I reacted in different situations and my communication during meetings builds greater awareness. This daily exercise and approach builds awareness, helping me become a better communicator

Do you have a set daily routine as a sales leader?

I do have a set routine that I follow daily which helps me as a sales leader. Reflecting on the day at the end of the day is important. As an Account Executive (AE), being effectively organized in your day is key to success.

This becomes even more important as a leader because your time can be chaotic. As an AE, you can plan your day and activities, but as a manager, balancing time is challenging. You'll be on sales calls, attend forecasting meetings, and need to set aside time for coaching and deep work on projects.

Organizing these days is crucial. My days and weeks vary, but I believe in starting the week and the night before each day by blocking out time to figure out what I need to accomplish. Staying focused on prioritization and organization is very important to me

Can you explain the concept of "Golden Hours" for sales teams?

The concept of 'Golden Hours' comes from a book on prospecting, possibly 'Fanatical Prospecting' by Jeb Blount. Golden Hours are times when prospects and clients are most receptive to messaging and when your energy is at its best.

These are the times best suited for revenue-generating activities. For example, if you're on the West Coast working with clients in the Central time zone, the period before lunch might be the perfect time to reach out. During Golden Hours, people are generally more available and at a good energy level. It's important to align these windows with your peak productivity times, whether you're a morning or night person.

Once you identify these windows, block them out and focus solely on high-priority tasks like contacting prospects and advancing sales deals. Avoid low-priority tasks like entering expenses, updating the CRM, or plugging in forecasts during these hours. Allocate other times of the day, like after 4 PM, for these activities. The key is to utilize Golden Hours effectively for the most impactful sales activities.

What are some common blind spots for new sales managers transitioning from an AE role?

A common blind spot for new sales managers transitioning from an AE role is the high degree of confidence from their success as AEs, which can lead to a one-size-fits-all approach. This mindset often results in micromanaging, as they might believe their way is the best and only way to be successful.

It's crucial to find a balance between providing support and guidance without dictating every aspect of their team’s day.

Another important aspect is not neglecting the human element of the manager-AE relationship. New managers often focus heavily on numbers and activity thresholds, potentially overlooking the importance of building strong relationships with their team.

Understanding your team deeply and forming strong partnerships early on is key. These are the major pieces of advice I would give to new managers to help them start on a better footing

What skills should AEs develop for successful team leadership?

Preparing for a managerial role is challenging because the nature of the work is quite different. The motivations, workflow, and outcomes vary significantly, making it difficult to gauge the success of a day as a manager.

However, focusing on building communication skills and developing relationships is crucial. As an AE, working cross-functionally with various internal teams, such as product or marketing, or mentoring junior reps, provides opportunities to develop these skills.

These skills are highly transferable to a managerial role, where managing a team of account executives involves applying the same communication abilities and relationship-building strategies.

Additionally, the better you perform as an AE and the more experiences you are exposed to, the more lessons and learnings you have to offer to your team.

Can you share insights into reversing a negative revenue trajectory to positive growth?

Before, our team was a true inside sales team, primarily focused on calls and emails and broad volume metrics that didn't accurately reflect the team's performance. Two reps could have the same methodology but vastly different success metrics. We made several changes:

Comprehensive Understanding of Activities: Instead of just tracking calls and emails, we looked at the consistency of outreach, the number of people reached out to at different accounts, and unique contacts and accounts over various time periods. This helped us understand the diversity and depth of outreach and whether it was leading to meetings.

Account Prioritization: We refined our Ideal Customer Profile (ICP) to target those who best fit our revenue model and have been strong partners. This involved providing different service levels to different partners, recognizing that not all customers are the same and have different revenue potentials.

By focusing on both prospecting with the new ICP and prioritizing customer service for existing partners, we achieved significantly positive effects.

How do you tailor your approach when developing managers versus individual contributors?

When developing individual contributors, the focus is more on hard skills, such as improving discovery, enhancing demo portions, and refining prospect emails. Coaching often centers around these hard, tactical skills. In contrast, when coaching managers and aiding their development, the emphasis shifts to soft skills.

This includes figuring out how to better coach and unlock potential in different types of reps, improving cross-functional work, and giving effective feedback.

Frontline managers often lack support and learn through trial and error, which is not always effective. In my role, I've focused on developing these managers, particularly their soft skills, recognizing that each manager has unique needs.

We also conduct a Manager Leadership Series most Fridays, where we discuss topics like delegation, feedback, or cross-functional work. In these sessions, we read articles and engage in discussions, somewhat like a mini book club. This not only helps in tackling challenges but also benefits the whole team and enhances my skills by learning from the managers' experiences

What advice would you give to sales leaders facing regionalization or reorganization of sales channels?

Dealing with regionalization or reorganization of sales channels is complex. Our team has undergone several iterations to determine what works best, which varies by industry, customer set, and performance areas.

For our company, as an inside sales solution, we identified a significant opportunity to move upmarket into a midmarket space, which resonated with some of our upper-end customers. By adjusting our outreach and target audience, we saw improved results.

Part of the strategy involves learning from experiences, testing, and iterating. It's crucial for reps to maintain focus and be effective. For example, some sales teams are divided by geographic territories or industries, each with its own merits.

We experimented with different geographic arrangements, considering the concentration and movement of marketers we sell to. A regional focus made sense for us, and we also considered an industry-based focus to enhance reps' domain knowledge in specific verticals.

As we moved into the mid-market, we recognized ongoing opportunities with small and medium-sized businesses (SMBs). We strategized on segmenting our team to target SMBs effectively. This approach involved responding to market feedback, testing different strategies, and ensuring our reps' efficiency.

What immediate challenges did you face when moving upmarket in terms of the sales process?

Moving upmarket in terms of the sales process presents challenges, particularly as this change is often gradual and can disrupt existing sales dynamics. For example, if a sales team or reps are accustomed to high volume and suddenly need to shift to less but higher quality activity, it can be difficult to measure and adapt to. This shift can feel strange for reps used to being at the top of the leaderboard who now find their position changing.

Mindset shift is a significant challenge. It's also difficult in reverse; if a mid-market team is asked to transition to an inside sales or SMB approach, suddenly needing to double their volume presents its own challenges.

To address these challenges, it's important to redefine key metrics and focus areas. This includes introducing new messaging and outreach methods. Heavy training and coaching are essential, working closely with the revenue operations and sales enablement teams.

This transition requires a strong commitment from the entire leadership group to consistently communicate the new direction, market opportunities, and focal points. It involves training, aligning product marketing, and monitoring new metrics on a daily and weekly basis to guide the team effectively into a different market segment.

What traits do you look for in new hires when building a team?

There are several traits I look for in new hires. Firstly, I want to understand their sales process and how they approach their day and week. Organization is crucial, so I assess how candidates build out their week, prioritize their activities, and whether they focus on revenue-generating activities. I'm interested in how they apply lessons from trainings or other learnings in their sales cycle, and how they handle challenges or losses.

It's important to see if these experiences led to any lessons or internal process improvements.

I delve into their learning process, organizational skills, and how they overcome challenges to gauge their growth and adaptability.

My team often hires people who are in the early stages of their sales career, typically three to five years in. It's essential that these individuals are still in growth mode, continuously learning and evolving, not just settling after moving out of an SDR role.

What resources would you recommend for continuous learning in sales?

The list of resources for continuous learning in sales is extensive and depends on your learning style. I personally enjoy podcasts, such as the Sales Leadership Podcast with Rob Gibson and Gong's podcast. Podcasts are a great way to learn without having to commit to reading books, which can be a bit dry for sales topics.

Another valuable resource is engaging with the LinkedIn community. Start by browsing your feed, searching hashtags related to sales or sales leadership, and following people who post content you find useful.

Engage in discussions and reach out to those you follow for virtual coffees or chats to discuss challenges they're facing. People on LinkedIn are generally welcoming and open to conversations and networking.

Ultimately, it's about finding the learning style that works for you. Whether it's podcasts, LinkedIn, subscribing to Harvard Business Review, reading books, or directly reaching out to people for their insights, each method has its value. Most professionals are willing to engage in conversations and share their knowledge.

We hope this enlightening conversation with Taylor has offered you valuable perspectives on sales leadership and professional growth.

Stay tuned for more such engaging and informative content that helps you grow and succeed in your sales career.

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