For many sales reps, the goal-driven approach to closing deals and hitting quotas can be a powerful motivator. But when a sales pro climbs the ladder to working with enterprise-level prospective clients, the sales cycle grows slower and the deals get bigger, necessitating a shift in approach.
Succeeding in enterprise sales requires patience, strategic thinking and a deep understanding of needs and trends as reps spend significant time researching their prospects, understanding each stakeholder’s priorities and building trust before they even discuss a contract.
According to reps from Trustpilot and Templafy, enterprise sales success isn’t just about closing the deal but creating a solution that aligns with the client’s long-term goals.
This demands an adaptable approach, as each client and contract may present unique challenges, and being an expert on both product and market trends is a must-have to establish credibility and influence decision-making at higher levels within an organization.
For many enterprise sales reps, the journey comes with challenges, but the rewards make it worthwhile. Enterprise sales offers the opportunity to make a significant impact on a client’s business, foster long-term partnerships and contribute to meaningful, large-scale projects.
Built In NYC heard from two seasoned enterprise sales reps about how they landed in enterprise sales and the lessons they’ve learned along the way.
Trustpilot is a global review platform that enables consumers to leave feedback about businesses, helping to build trust and transparency between companies and customers.
Tell us about your journey into enterprise sales.
When I joined Trustpilot over six years ago, I started with the ambition to continuously grow both personally and professionally. Moving into enterprise sales felt like a natural step — I enjoy building strategic relationships and solving complex challenges for businesses.
One of the most memorable experiences has been securing a partnership with a major industry player, which involved months of collaboration across teams. When it finally came through, the entire team rallied to celebrate, making me feel truly valued and appreciated. It was an incredible reminder of how Trustpilot encourages teamwork, empowering us to provide value for customers at every touchpoint.
“Moving into enterprise sales felt like a natural step — I enjoy building strategic relationships and solving complex challenges for businesses.”
What is the most challenging aspect of enterprise sales? What about the most rewarding part?
Enterprise sales comes with its share of challenges — primarily the long sales cycles and intricate decision-making processes. Staying patient and persistent is key, but what makes it manageable is the strong support network at Trustpilot. From working with my team to working with solutions engineers, customer success managers and more, I can always rely on my colleagues and know they’re willing to help. The most rewarding part is seeing how our solutions truly help businesses enhance their reputation and grow, especially when you witness the impact over time.
What is the most important lesson you’ve learned from your time working in enterprise sales?
The biggest lesson I’ve learned is the importance of adaptability. Every enterprise client has unique needs, so being flexible and open to feedback is crucial. My advice for anyone transitioning from SMB or mid-market sales is to embrace continuous learning and understand that success doesn’t always come quickly. It’s about playing the long game — building trust and positioning yourself as a strategic consultant to businesses to ensure we’re helping the customer find a solution that fits their needs.
Templafy is a content management and document automation platform designed to streamline the creation, management and distribution of business content across its clients’ organizations.
Tell us about your journey into enterprise sales.
I started my career in a sales development program for a large Fortune 500 company. One of my roles was in inside sales, supporting a seasoned field sales rep that was selling to large enterprises. I knew eventually I wanted to be the strategic relationship executive in a similar capacity, but first I wanted to transition to a SaaS business and get experience owning clients on my own.
I took a job in New York as a customer success account manager for a medium-sized SaaS marketing company, where sales were relatively transactional and less strategic, but it got me a lot of experience in closing deals and owning relationships with customers. After a few years in management there, I was ready to go back to an individual contributor role where I would have the opportunity to cut my teeth selling to large enterprises in the United States.
Cue Templafy.
What is the most challenging aspect of enterprise sales? What about the most rewarding part?
I wanted to sell to some of the biggest companies in the world because I knew it would be a challenge. It would take more than just hard work — the role required understanding major initiatives, stakeholder mapping and relationship building across the board.
“I wanted to sell to some of the biggest companies in the world because I knew it would be a challenge.”
What is the most important lesson you’ve learned from your time working in enterprise sales?
The hardest part about selling to large organizations is navigating their internal politics. The larger the organization, the more hurdles there are to go through and the more people are involved in decisions — and, because of that, things move slower.
It’s absolutely critical to build relationships across all parts of the organization — your buyer, other parts of the business, procurement, operations, IT. Every time you’re introduced to somebody, you have an opportunity to leave a positive impression and build business trust. It’s the most rewarding part for me — catching people off-guard with how happy you are to be speaking with them and pulling them out of their (sometimes) mundane day-to-day work creates excitement about what our organizations can accomplish together.
