With rejection and high-pressure performance as just a part of the job, a career in sales isn’t for the faint of heart.
Enterprise sales is even more challenging: Aligning multiple stakeholders, navigating legal and security reviews and crafting multi-year agreements are a daily challenge that require grit and finesse. Luckily, the two enterprise sales professionals we spoke with have both of those qualities in spades.
Curious about a career in enterprise sales? Read on to get an inside look at what it takes on these growing SF teams.
Notion is the AI workspace where teams and AI agents get more done together.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
As an enterprise account executive at Notion, I lead strategic sales cycles with some of our largest global customers, focusing on organizations evaluating Notion to centralize knowledge, projects and AI-powered workflows. My role spans full-cycle enterprise sales — from initial outreach and discovery to legal/security reviews and multi-year partnership negotiations.
Day to day, I manage a mix of prospect and customer calls, including technical deep dives with IT and InfoSec, executive demos for C-suite stakeholders and business case reviews for cross-functional pilots. I partner closely with solutions engineering, legal and customer success to design tailored proof-of-concepts, navigate MSAs/DPAs and build long-term expansion strategies.
Beyond calls, I spend time building proposals in Notion, running internal deal reviews and aligning with product and marketing to capture feedback from the field — all with the goal of helping large enterprises consolidate fragmented tools and adopt Notion as their connected workspace
Tell us about your professional background. What made you want to work in enterprise sales and how did you break into selling for that market segment?
I’ve been at Notion for over three years, where I’ve helped build and scale our go-to-market motion across both the mid-market and enterprise segments. Early on, I focused on growing Notion’s mid-market business — building repeatable sales motions, refining messaging and helping design the processes that bridged product-led growth to strategic sales. As Notion evolved upmarket, moving into enterprise sales felt like a natural next step.
I’ve always been drawn to more strategic, complex deals — the kind that require deep discovery, creative problem-solving and long-term partnership building. Enterprise sales allows me to engage at that level: aligning multiple stakeholders, navigating legal and security reviews and crafting multi-year agreements that drive lasting impact for our customers. What keeps me motivated is the opportunity to build genuine relationships and help large organizations transform how they work, all while continuing to shape Notion’s presence in the enterprise space.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Breaking into enterprise sales takes grit, resilience and a willingness to constantly adapt. The deals are more complex and the cycles are longer — but that’s what makes it rewarding. At Notion, our sales motion evolves quickly as the product and market grow, so the people who succeed are the ones who stay curious, think on their feet and don’t get discouraged when things change or don’t go their way.
Stand-out enterprise reps are the ones who put in consistent effort — not just during the exciting parts of a deal, but in the quiet moments of research, follow-up and alignment. They balance persistence with patience, understand how to navigate multiple stakeholders and earn trust by adding value at every step. Above all, they see each deal as a partnership, not a transaction — and that mindset is what drives long-term success.
Motive is a tech company that creates products meant to improve the safety and productivity of the physical economy.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
At Motive, I lead enterprise sales, customer success and account management. My focus is on building an environment where our teams can succeed — partnering with executives to define strategy, allocate resources and manage the P&L for our division.
As a high-growth company, revenue generation remains top priority, so I stay deeply involved in strategic deals. I provide executive sponsorship, joining calls with C-level leaders at key prospects to align on vision and partnership. I also lead strategic deal reviews, helping teams think beyond “closing” to emphasize differentiation and long-term value.
Internally, I work cross-functionally with product, marketing and finance to remove barriers and ensure our teams can deliver on every promise we make.
Our enterprise reps operate very differently from SMB or mid-market teams — they multi-thread across 10 to 20 stakeholders per account, build detailed ROI and total cost of ownership models and orchestrate complex internal coordination across solution engineering, legal and success teams to move multi-million dollar opportunities forward.
Tell us about your professional background. What made you want to work in enterprise sales and how did you break into selling for that market segment?
My path to enterprise sales leadership was non-traditional, which I’ve found to be a significant advantage. I didn’t start my career carrying a quota. I began in management consulting, focusing on go-to-market strategy — advising large companies on how to structure sales teams, price products and enter new markets. I built the same business cases and ROI models that drive major enterprise deals today.
While I loved the strategic challenge, I eventually felt the pull to move from advising to doing. That led me into tech as a sales engineer — a critical move that introduced me to sales and taught me to speak with absolute credibility. I learned not only to build and demo solutions but to align them to real business value.
My “break-in” moment came from that sales engineer role. I was already co-selling complex deals and realized I loved navigating both financial and technical challenges. My consulting background gave me financial acumen and my sales engineer experience gave me technical credibility — the two skills that define a great enterprise rep.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
My advice is to see this as a game of acquiring skills, not just titles. Starting as an SDR or BDR is great, but if you’ve begun your career elsewhere, don’t be afraid to take a non-traditional path into sales through intermediate steps. Think about the next step forward and how to hone your skillset. A sideways move into a role like sales engineer or customer success manager can be the perfect slingshot. Those roles give you visibility into what it looks like to be an enterprise seller before carrying a quota.
What Motive Technologies looks for in interviews for sales jobs
“When I’m interviewing, I look for a few key traits — it’s rarely the ‘fast-talker,’” said SVP of Enterprise Sales Kate Woelffer.
- Deep Curiosity: A stand-out rep acts like a strategic partner, asking “why” five times to get to the root of a problem and deeply understanding the client’s industry, competitors and internal politics.
- Masterful Orchestration: Enterprise sales is a team sport. The best reps are “quarterbacks” who rally internal teams without authority.
- Proactive Urgency: Enterprise deals are marathons, but won with action. Top reps drive timelines, multi-thread and clear roadblocks.
