Nayte Olukoya: From The Bachelorette to SaaS Sales Success
Nayte Olukoya has made a name for himself in two very different worlds—reality television and the competitive tech sales industry. Known to millions as the winner of Michelle Young’s season of The Bachelorette, he has since carved out a thriving professional career in SaaS sales, helping businesses embrace digital transformation. Today, Olukoya’s journey combines personal resilience, high-profile relationships, and professional growth across companies like Box, TeamSnap, DISCO, and Indeed.
This article explores Nayte Olukoya’s career path, education, television fame, relationships, and current professional life, offering an in-depth look at how he transitioned from the spotlight of reality TV to success in the corporate world.
Early Life and Education
Academic Background
Babatundé Robert Nathaniel “Nayte” Olukoya was born in Winnipeg, Canada, and later moved to the United States for his education. He attended Eastern Washington University from 2014 to 2019, where he earned a Bachelor of Business Administration (BBA) with a concentration in Business Administration and Management.
In addition to his business studies, he pursued a minor in African American History, showing his interest in cultural and social studies alongside business strategy. This educational foundation gave him the tools to enter the competitive world of sales, where he would later build an impressive career.
Professional Career Journey
Nayte’s career path reflects persistence, adaptability, and growth across various industries.
AT&T: The Starting Point
From 2015 to 2018, Nayte worked as a Sales Representative at AT&T in Cheney, Washington. During this role, he developed fundamental sales skills including negotiation, customer relationship management, and qualifying opportunities. This was his first step into professional sales, giving him a platform to advance further.
PRESS: Customer-Facing Experience
Between 2018 and 2019, Olukoya worked as a bartender at PRESS, located in Spokane, Washington. While this may seem outside his long-term career goals, it was an important step in honing interpersonal skills, relationship building, and understanding client service in a fast-paced environment.
Indeed: Entering SaaS Sales
In 2019, Nayte transitioned into SaaS sales by joining Indeed.com in Austin, Texas.
-
He began as an Account Executive (2019–2021).
-
Quickly promoted to Senior Account Executive (2021).
At Indeed, Nayte excelled in outbound sales, product demonstrations, and relationship management. This experience introduced him to the world of enterprise technology and digital solutions, setting the stage for future leadership roles.
DISCO: Climbing the Sales Ladder
From October 2021 to July 2023, Olukoya worked as a Senior Account Executive at DISCO, a legal technology company. Here, he sharpened his ability to manage complex sales cycles, consultative selling, and SaaS account management. His skills expanded to include:
-
Business-to-business (B2B) solutions
-
Sales forecasting
-
Cold calling and lead qualification
-
Strategic partnerships
This role allowed him to develop confidence in managing high-value accounts and strengthened his position in the SaaS industry.
TeamSnap: Expanding Horizons
In July 2023, Nayte joined TeamSnap as an Account Executive, a role he still holds as of 2025. Based in Austin, Texas, his responsibilities include driving revenue growth, managing client relationships, and helping organizations streamline operations through SaaS tools. His tenure at TeamSnap has lasted more than two years, proving his ability to deliver consistent results.
Box: A New Chapter
Most recently, in January 2025, Nayte took on the role of SMB Account Executive II at Box, a leading company in cloud storage, AI, and collaboration solutions. This position highlights his progression into enterprise-level SaaS sales. At Box, he supports businesses in accelerating digital transformation, focusing on:
-
Cloud adoption strategies
-
Collaboration tools for remote teams
-
AI-driven solutions for productivity and data security
His career trajectory demonstrates continuous growth, from entry-level sales to high-impact roles in major SaaS organizations.
Skills and Expertise
Throughout his career, Nayte Olukoya has developed a diverse set of skills, including:
-
Creative Problem Solving
-
SaaS Sales & Account Management
-
Negotiation & Strategic Partnerships
-
Sales Target Management & Quotas
-
Lead Qualification & Forecasting
-
Consultative Selling & Storytelling
These skills make him a strong force in technology sales, capable of managing complex business relationships and driving long-term value.
The Bachelorette Fame
Michelle Young and Nayte Olukoya
In 2021, Nayte rose to national fame when he appeared on Season 18 of The Bachelorette, starring Michelle Young. He received the first impression rose and ultimately won Michelle’s final rose at the end of the season. The couple got engaged on the finale, making history as the first Black couple to become engaged in the Bachelorette franchise.
Their relationship was highly celebrated, with plans for moving in together and even financial support from the show’s producers for their future. However, by June 2022, Michelle Young and Nayte Olukoya announced their breakup, citing challenges in making their relationship work outside of the show.
Nayte Olukoya’s Girlfriend After Michelle
Following his split from Michelle Young, Nayte took time away from the public spotlight. In February 2024, he confirmed a new relationship with Allyssa Malony, a social media manager based in Los Angeles. He publicly shared their relationship on Instagram during Valentine’s Day 2024, making it official.
This “hard launch” of his new romance marked a new chapter in his personal life, showing his readiness to move forward after the highly publicized breakup with Michelle.
Balancing Fame and Career
Nayte Olukoya stands out as someone who successfully navigated life after reality TV. Many former contestants struggle to balance public attention with building stable careers, but Nayte transitioned seamlessly. His return to tech sales shows his ability to stay grounded, focus on professional goals, and build credibility beyond television fame.
Conclusion
Nayte Olukoya’s story is one of adaptability, resilience, and reinvention. From his beginnings in sales at AT&T to working at major SaaS companies like Indeed, DISCO, TeamSnap, and Box, he has consistently grown his professional career. His personal journey—rising to fame on The Bachelorette, his engagement to Michelle Young, their eventual breakup, and his new relationship with Allyssa Malony—adds depth to his profile, blending personal challenges with professional victories.
Today, Nayte Olukoya is more than a former reality TV star. He is a seasoned Account Executive specializing in SaaS sales, cloud solutions, and digital transformation. His career demonstrates how determination and adaptability can lead to success both in the public eye and in the professional world.
