Career Progression in Sales: Moving into Leadership or Enterprise Sales?

You’ve been a performer in sales, and it’s time to make a decision. Will you take that promotion into leadership, or will you remain an individual contributor and move up to Enterprise? Both options offer unique opportunities for growth and development. SalesFirst Recruiting will help you consider your strengths, aspirations, and personal preferences before choosing your career trajectory.

Leadership vs Enterprise Sales

Natural Leadership Abilities: Some sales reps possess innate leadership qualities, such as strong communication skills, the ability to inspire and motivate others, and a natural inclination towards mentoring and coaching. These individuals have a knack for guiding and developing teams, making a transition into leadership roles a seemingly natural fit. That said, natural leadership skills also come in very handy as an Enterprise rep. Enterprise reps are often tasked with “Quarterbacking” a team of specialists focused on closing major accounts.

Verdict: Draw. Having natural leadership abilities are helpful -and necessary- in both career paths. Whether leading a team as a sales leader or quarterbacking a team of specialists in Enterprise sales, strong communication skills, the ability to inspire and motivate others, and a natural inclination towards mentoring and coaching are valuable.

Desire for Influence and Impact: Sales reps who aspire to have a broader influence and make a significant impact on the overall success of an organization often find fulfillment in leadership positions. Leadership roles provide opportunities to shape sales strategies, drive team performance, and contribute to the overall growth and success of the company. But of course the same can be said for the individual contributor who hunts whales for the organization. Closing strategic accounts typically requires buy-in and negotiations from major stakeholders in each party.

Verdict: Draw. The desire for influence and impact is necessary for both roles. A mature approach, intelligence, and teamwork will earn you influence and impact no matter what role you select.

Skill Set Expansion: Moving into leadership allows sales professionals to expand their skill set beyond individual selling. They gain experience in strategic planning, team management, performance evaluation, and decision-making. These skills not only enhance their career prospects but also provide a solid foundation for future growth within the organization. Enterprise sales reps must also seek to expand their skill sets. With ever-changing market trends and customer demands, sales reps need to be able to adapt to new situations and create value for their clients. This involves developing new skills such as analytical thinking, understanding of market trends, and strong communication skills to convey complex ideas to decision-makers. And of course, the ability to reach decision-makers in enterprise organizations is a science within itself.

Verdict: Draw. It’ll take skill set expansion for both leadership and moving up-market in sales. Leading reps requires its own unique set of abilities that slightly differ from those needed to close enterprise deals. Either way, individuals must hone a diverse range of skills such as effective communication, strategic thinking, and adaptability.

Long-Term Career Development: For individuals who are looking for a long-term career path, transitioning into leadership roles can offer greater stability and progression. Leadership positions often come with increased responsibility, higher compensation, and the potential for executive-level roles in the future. But don’t count out Enterprise Sales as a career path for long-term career development. Long-term career development often leads to leadership roles which offer stability, progression, and potential future executive-level positions.

Verdict: Leadership. Both Leadership and Enterprise Sales offer fantastic long-term career development, but taking a leadership role opens up important doors to executive positions.

Hunter Mentality and Independence: Sales reps who thrive on the excitement of pursuing new business opportunities, enjoy building relationships with key clients, and prefer the freedom and independence of managing their own accounts will undoubtedly find Enterprise sales roles more suitable.

Verdict: Enterprise Sales. We uncover countless sales leaders who long for the days of being responsible for only themselves while earning the same or even better pay. Some sales leaders do find renewed energy in the freedom to focus solely on their own performance and ultimately find it to be a rewarding change of pace. However, transitioning back to an individual contributor role can be a challenge. After years of leading and strategizing, going back to a sole focus on personal performance can be difficult and may even seem like a step down.

Focus on Complex Sales Cycles: Enterprise sales typically involves longer and more complex sales cycles. Sales reps who enjoy navigating intricate deals, handling sophisticated customer requirements, and leveraging their deep product knowledge to solve complex challenges may find this arena more fulfilling. Sales Leaders don’t have to give this up entirely, however. Sales Leaders often have the flexibility to spend their time on the deals that interest them.

Verdict: Enterprise Sales. While leaders often get to spend time on areas of their choosing, the likelihood they get pulled away to extinguish other fires is still there.

Financial Incentives: This is a generalization, but the way we describe the difference here is that Sales Leaders tend to have a higher floor, and Enterprise Sales Reps tend to have a higher ceiling. It all depends on your unique compensation plan, and it also depends on what roles you really enjoy.

Verdict: Not enough information. Sorry for dodging this one, but professionals will earn more where they are most skilled. There are too many factors to consider when comparing salaries of professionals. A person's level of experience, demand for their skills, geographic location, and the industry they work in can all come into play. Therefore, it is challenging to make a straightforward statement, but it typically holds that where one has particular skills and ability, there are potentially more significant earning opportunities.

Desire for Specialization: Some sales reps prefer to develop deep expertise within a specific industry or market segment. Transitioning up-market allows them to focus their efforts on a particular niche, building specialized knowledge and becoming a trusted advisor to high-value clients. Leaders aren’t always afforded this luxury.

Verdict: Enterprise Sales. Clear winner here- if you really want to specialize in something, start off by remaining an individual contributor until a specific, unique leadership opportunity opens for you.

Personal Growth and Learning: Moving up-market to Enterprise can expose sales reps to new challenges, industries, and high-level decision-makers. This presents opportunities for personal growth, learning, and expanding professional networks, which can be rewarding for individuals seeking continuous development and new experiences. But few things can compare to the journey of leadership where leaders encounter deep problems and lessons on an almost daily basis.

Verdict: Leadership. In addition to providing valuable experience in an ever-evolving sales landscape, it also offers immense potential for career advancement and success.

The Final Verdict

There isn’t one. The decision between taking a promotion into leadership or remaining an individual contributor and moving up to Enterprise sales is a personal one that depends on individual strengths, aspirations, and preferences. Both options offer unique opportunities for growth, development, and earning opportunities.

Remember, it's not just about reaching the destination, but enjoying the journey too! Take time to appreciate what you're doing, learn as much as you can, and embrace the ride.

Ask SalesFirst Recruiting for Help!

If you are ready for a new opportunity, we are available to help you. With our expertise and deep understanding of the sales industry, we'll provide you with valuable insights and guidance tailored to your unique situation. We'll help you explore both options thoroughly, weighing the pros and cons to ensure you make an informed decision that aligns with your goals and aspirations.

Don't let this decision overwhelm you. Reach out to SalesFirst Recruiting today, and let us support you in choosing the career trajectory that will maximize your potential and lead you to long-term success. Your next great opportunity awaits, and we're here to help you seize it!