The first day in an enterprise sales role is a little like being a painter and looking up at your first large-scale, empty and daunting canvas.
Artists who make this leap can tell you — it requires some strategizing.
Scaling any effort requires that you start thinking in stages. Project planning is as much a key part of grand works of art as much as years of practice and natural talent.
A talented enterprise salesperson knows this: enterprise sales requires its own unique strategies.
Built In Chicago spoke with two sales leaders who each shared how they moved to the enterprise level, what tactics helped them get there and what strategies help them succeed.
Both agreed that interpersonal relationships are the most important aspect of sales. Sara Oberst, vice president of growth at Bounteous x Accolite, said, “Enterprise sales is never transactional; success depends entirely on building and nurturing genuine relationships with people, not just companies.”
But the two had different opinions on how to best approach a masterpiece-level deal. Their collective tips include: stay organized; break the deal into smaller milestones; hone an ability to absorb vast, highly-complex information and distill it into clear, impactful insights; and, perhaps most importantly, don’t get too bogged down in the tech that you lose sight of human connection.
Both agreed, though, that enterprise sales is worth it.
“Securing large enterprise accounts can be career-defining, offering a sense of prestige that comes with working with well-known brands and high-profile companies,” said Chris Maguire, national account executive with SpotHero. “These wins often open the door to further opportunities in the sales world.”
Bounteous x Accolite is an end-to-end digital transformation services consultancy that partners with leading brands around the globe to co-innovate and drive exceptional client outcomes.
Tell us about your journey into enterprise sales. What made you want to sell to enterprise customers, and what has been a memorable experience so far?
I began my career as a content strategist at a healthcare and pharmaceutical experience agency, where I focused on gaining a deep understanding of the complexities of clients’ products and mapping out buyer decision-making and purchasing journeys.
As my career evolved into enterprise sales, I maintained my commitment to learning the intricacies of clients’ businesses, products and buyer journeys. This ability to absorb vast, highly-complex information and distill it into clear, impactful insights has become my superpower as an enterprise seller. Over the last decade, I’ve honed this skill through my work partnering with, selling and delivering large-scale digital transformation and emerging technology initiatives to global enterprise clients.
What is the most challenging aspect of enterprise sales? What about the most rewarding part?
The greatest challenge — and the most rewarding part of my career — is the dynamism of enterprise consulting. Each client faces unique growth challenges, from both their market and within their organization. I’m constantly learning and adapting to meet these unique challenges and goals by bringing a fresh perspective to each relationship and leveraging the incredible talent of Bounteous x Accolite’s subject matter experts to drive successful outcomes for our clients. Sometimes, this involves identifying emerging technologies that solve previously unsolvable problems. At other times, it’s more about peeling back the layers to uncover the root issues hindering growth and crafting strategies that refocus on doing the basics better and delivering on core customer needs.
“The greatest challenge — and the most rewarding part of my career — is the dynamism of enterprise consulting.”
What is the most important lesson you’ve learned from your time working in enterprise sales. What advice would you give to a sales rep looking to make the leap into enterprise accounts?
Technology is always evolving. There’s a lot of hype and it can be easy to lose sight of what really makes an impact. The beginning and the end of every growth strategy must be grounded in people. If you lose sight of the human element in the equation of any business strategy — no matter what technology you are implementing — your strategy is destined to fall short. My sales strategy is firmly rooted in people, the client, their stakeholders and the customers they serve. Enterprise sales is never transactional; success depends entirely on building and nurturing genuine relationships with people, not just companies.
SpotHero is a digital parking company and an independent off-street parking marketplace.
Tell us about your journey into enterprise sales. What made you want to sell to enterprise customers, and what has been a memorable experience so far?
Enterprise sales has been part of my career portfolio for almost 20 years. While one of the greatest challenges in sales, it still captivates my attention. For those like me who thrive on working toward big wins and closing transformative deals, the enterprise space offers a level of reward and personal satisfaction that smaller-scale sales may not.
I also enjoy the intellectual stimulation it provides. The constant learning and adaptation required to navigate complex sales cycles keeps me sharp.
Some of my most memorable experiences in this field have come from building long-term relationships. Selling to enterprise clients is not about one-off transactions; it’s about creating meaningful relationships that lead to future opportunities, upselling and renewals. I find this deeper, ongoing engagement with enterprise customers particularly fulfilling. It also enhances credibility and reputation.
What is the most challenging aspect of enterprise sales? What about the most rewarding part?
The most challenging part of enterprise sales is managing long sales cycles, multiple stakeholders and internal coordination. Overcoming this requires building strong relationships, staying organized and maintaining clear communication.
Taking on Enterprise Challenges
Maguire’s strategies to tackle challenges like managing long sales cycles, multiple stakeholders and internal coordination:
- Clear communication and documentation: Align internal stakeholders early. Clear, documented agreements and timelines ensure everyone is on the same page.
- Strategic problem-solving: Enterprise customers face complex challenges, requiring innovative solutions. This is an opportunity to work closely with decision-makers, understand their pain points and design impactful solutions that contribute to their success.
- Build relationships and trust: Consistent communication with stakeholders is key. Understanding each decision-maker’s goals helps tailor your approach.
- Manage expectations and set milestones: Break the deal into smaller milestones. Celebrate small wins to maintain momentum and interest.
The most rewarding part is solving complex problems and building long-term relationships. Offering tailored solutions that improve the client’s operations is deeply satisfying.
What is the most important lesson you’ve learned from your time working in enterprise sales. What advice would you give to a sales rep looking to make the leap into enterprise accounts?
The most important lesson I’ve learned in enterprise sales is the power of authentic relationships. It’s not just about selling a product but understanding your customer’s needs and becoming a trusted advisor. By focusing on genuine connections, you can navigate challenges and close deals.
My advice for sales reps making the leap is that enterprise sales is more complex than selling to small and mid-sized businesses or mid-market accounts. Expect longer sales cycles, more decision-makers and thorough evaluations. Shift your mindset to focus on the value and business impact of your solution, not just features. Think bigger — how does it drive efficiencies, revenue or scale?
Master strategic selling by understanding your customer’s objectives and mapping out the decision-making process. Tailor your approach to key stakeholders’ priorities, whether cost, efficiency, security or scalability. Deepen your industry and product knowledge to position your solution effectively.
Build a strong network — attend conferences, engage on LinkedIn and seek industry insights. Stay patient, persistent and positive. Success comes with time and effort.
