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In this episode, Rosa Campagna tells us about what it actually takes to win at the highest level in enterprise and why patience, hospitality, and influence may be more important than any sales technique.
Rosa Campagna is the number one top performing sales rep globally at OneStream Software for FY25, hitting 428% of quota attainment in one of the most competitive enterprise sales organizations in the market. She works with customers ranging from $4 to $40 billion in revenue and has built her success on three principles: knowing how people think and feel, mastering the internal sale, and refusing to put enterprise customers to bed in pursuit of short-term wins.
Rosa came to sales by accident. She thought she wanted to be Samantha from Sex and the City, landing somewhere in PR and marketing. A theater kid at heart, she eventually found her way into consulting and professional services in the Salesforce ecosystem, survived multiple layoffs during a volatile period of acquisitions, and ultimately made the bet that she was better at selling a thing than selling the process to build one. That pivot to software sales at OneStream, combined with the mentorship of John Davis and a relentless show must go on mentality she calls the Rosa Factor, is what got her to the top of the global leaderboard.
This episode was sponsored by: Nooks
Nooks – One unified workspace where reps work alongside AI agents for every task.
What We Covered:
[00:00:00] Rosa’s three success factors: client relationships, knowing your internal engine, and not putting your enterprise customers to bed
[00:00:41] The internal sale explained: how to win internally the same way you win externally, and why finance and legal deserve the same energy as your best prospect
[00:03:06] The two to three year enterprise buying cycle philosophy and why taking a smaller deal now can produce significantly larger results later
[00:04:07] The John Davis connection: how Rosa’s first manager at OneStream set the tone for how she thinks about long-term deal strategy, and the first deal advice that helped her win Rookie of the Year
[00:07:51] Color-coding the calendar as a time management and self-awareness tool: yellow for internal, green for existing customers, pink for new logos
[00:10:33] What OneStream does, who Rosa sells to, and what the show must go on mentality really means in practice
[00:12:09] The Rosa Factor: the combination of performance background, likeability, tenacity, and relentless preparation that defines her approach
[00:13:14] Results: 428% of quota attainment, neck and neck with Garrett for the global top spot in a highly competitive sales org
[00:13:42] Career origin story: from marketing and PR aspirations to consulting in the Salesforce ecosystem, multiple layoffs, and the pivot to software sales
[00:16:30] How Rosa would approach starting a sales career in today’s environment: get clarity on what you want to sell, read your network’s temperature, build moats, and demonstrate your ability to pivot
[00:20:34] Favorite sales story: working with a large asset manager, the patience it required, and what it taught her about the long game
[00:28:38] What challenges her most day to day and how she manages the temperance of staying internally focused without losing sight of the external relationship
[00:40:09] Typical day in the life: a 60/40 split between internal work and customer-facing time, and how she structures that intentionally
[01:00:27] Tools and the AI question: Salesforce, Gong, Microsoft Teams as a client engagement channel, and why the most important AI question is not which tool to use but where AI already lives inside the tools you have
[01:13:56] Why hospitality is a core part of her sales strategy and how the Nonna Effect translates directly into client influence and pipeline
[01:17:20] The enterprise customer dating analogy: first deal is a first date, second deal puts a ring on it, third deal is the wedding. Why you have to earn the big deal.
[01:19:09] The clock always resets: the moment she held her 2025 Global Rep of the Year award and reminded herself she was sitting at zero percent
[01:19:52] Easter eggs in the pipeline: why she deliberately designs her book of business so that future wins are already in motion
[01:23:41] The water cooler effect and why getting inside your customer’s native environment, whether Teams, Slack, or an in-person dinner, changes everything
[01:30:14] Three pillars of influence: the go-to-war champion, the remember-that-time relationship, and knowing somebody who knows somebody
[01:34:44] Soapbox: the eight-year-old and the eighty-year-old, the importance of staying playful, and why thinking about the most irresponsible option often reveals the most creative path forward
[01:38:49] Actionable challenge: find something that makes you laugh before you try to solve your next hard problem
Quotes:
“Client relationships number one. Knowing your internal engine number two. And don’t put your customers to sleep number three.” (00:03:43)
“Even Baryshnikov does pliés before he does anything else. It just doesn’t matter how good you are. Everybody needs to start with foundations and do preparation.” (00:08:59)
“The show must go on mentality is probably the Rosa Factor. Factoring in not just who I am at OneStream and what I sell, but what got me to be sitting at this moment right now.” (00:12:09)
“I want people to feel like when they sit in my company, they’re sitting at a Sunday dinner with my nonna.” (01:14:23)
“When they buy from you the first time, they’ve basically just said, okay, I’ll date you. When they buy from you the second time, they’re like, all right, I really like you. I’ll give you a ring.” (01:17:20)
“Don’t put your enterprise customers to bed. Don’t chase the commission. Chase the long haul.” (01:18:35)
“I won this award. 428% quota attainment. And when I got that award, do you know what my quota was at? Zero. Who cares about 428%? Last time I checked, I’m sitting at zero.” (01:19:09)
“There is the eight-year-old version of you and then there is the 80-year-old version of you. When you stop having fun or creating moments of play, nothing you do will ever feel like living.” (01:34:59)
“If you’re always thinking about being the most responsible, you’re probably not thinking big enough. Think about what the most irresponsible thing would be and try and find something in the middle.” (01:36:14)
Resources Mentioned:
OneStream Software
Irfan Jafar: Sales Success Stories Episode 115: top1.fm/115
The Sopranos
Dungeon Crawler Carl (audiobook series)
Sales Success Summit: top1.fm/summit
Connect with Rosa Campagna on LinkedIn
Sales Success Stories is part of the Sales Success Media family hosted by Scott Ingram