SaaSy Talk Unfiltered: The Inspiring Journey of Roi @ Uptick

An in-depth exploration of the growth and success of Uptick, featuring insights from Roi, the CRO of the company.

LISTEN to the full chat

S01.E02

In this thought-provoking interview, we delve into the remarkable journey of Uptick, a rapidly growing company in the software industry. Roi, the Chief Revenue Officer (CRO) of Uptick, shares his experiences and insights on various topics, including the early days of the company, the importance of sales roles, the challenges of international expansion, and the key metrics for success. Through his candid and honest responses, Roi provides valuable lessons and perspectives for anyone interested in sales, marketing, and scaling a business.

From Luck to Opportunity: The Early Days of Uptick

Roi's Serendipitous Encounter with Uptick

Roi begins by recounting how he stumbled upon Uptick during his university days. Working part-time at a property management company, he discovered the software Uptick, which was being used by a competitor fire company. Intrigued by the potential of the software, Roi reached out to the founder, Aiden, and convinced him to hire him. This stroke of luck led Roi to become the first commercial hire at Uptick.

Embracing the Challenge of Sales

As a 22-year-old fresh out of university, Roi was thrust into the world of sales. His initial role was to facilitate the founder's sales pitches, organizing meetings and ensuring everything ran smoothly. Despite his lack of experience, Roi embraced the challenge and learned the ropes of sales through trial and error. He emphasizes the importance of being relentless and consistent in sales, as well as the value of understanding the difficulties faced by sales development representatives (SDRs) and business development managers (BDMs).

Challenges of Scaling and Onboarding

As a company grows, scaling the sales team and onboarding new members can be challenging. Matt acknowledged that many organizations struggle with maintaining consistency and alignment as they bring on new hires. He stressed the importance of providing consistent training and development opportunities for all team members, regardless of their role. Matt mentioned that Sales Assembly is transitioning from training for job titles to training for skills, such as storytelling and negotiation. This shift will allow them to provide more impactful and comprehensive training to their clients.

Learning by Doing: The Playbook for Success

Picking Up the Phone: Roi's Journey to Sales Mastery

When asked about the early days of Uptick and the development of a sales playbook, Roi admits that he had no idea what he was doing. However, he quickly realized the importance of picking up the phone and making calls. His role was not to sell the software directly, but to facilitate the founder's sales process. This hands-on experience taught him the challenges faced by SDRs and BDMs, and he gained a deep appreciation for their hard work and resilience.

Managing SDRs and BDMs: The Uphill Battle

Roi emphasizes the difficulty of managing SDRs and BDMs, as their role requires high energy levels and the ability to handle rejection on a daily basis. He believes that many managers underestimate the challenges faced by these roles and encourages leaders to provide support and understanding to their sales teams. He also advises against outsourcing everything, as there is value in being involved in the day-to-day activities and understanding the nuances of the sales process.

From Amateur to Expert: The Founder-Led Playbook

Roi's Journey from Novice to Sales Expert

Reflecting on the early days of Uptick, Roi acknowledges that he was an amateur with no knowledge of software sales. However, he attributes his success to his willingness to try new things and learn from his failures. He believes in the power of learning by doing and encourages others to take initiative and embrace new opportunities.

Building a Strong Team: The Key to Success

Roi's Journey from Novice to Sales Expert

Reflecting on the early days of Uptick, Roi acknowledges that he was an amateur with no knowledge of software sales. However, he attributes his success to his willingness to try new things and learn from his failures. He believes in the power of learning by doing and encourages others to take initiative and embrace new opportunities.

Scaling the Business: Conquering the UK Market

Choosing the UK: Uptick's Strategic Expansion

As Uptick experienced success in the Australian market, the company set its sights on international expansion. Roi explains the decision-making process behind choosing the UK as their next target market. The UK was a natural fit due to its similarities to the Australian market in terms of industry practices and competitor landscape. Roi also highlights the importance of focusing on a niche market within the UK, which allowed Uptick to stand out and provide specialized software for a specific industry.

Overcoming Challenges: Establishing a Presence in the UK

Roi shares the challenges faced during the UK expansion, including the need to onboard new customers and establish a presence in a new market. He emphasizes the importance of building strong relationships with early customers and ensuring their success. By focusing on a small number of customers and making them advocates for the company, Uptick was able to establish a strong foundation in the UK market.

Adapting to Change: Uptick's Response to COVID-19

Navigating the Impact of COVID-19

The COVID-19 pandemic brought about significant changes in the way Uptick operated. Roi discusses the shift to remote work and the impact it had on the sales process. He highlights the increased efficiency of virtual meetings, allowing for more meetings to be conducted in a day. Roi also emphasizes the importance of maintaining a healthy sales pipeline and the need for consistent activity to drive revenue generation.

Customer Success: The Cornerstone of Uptick's Growth

The Importance of Customer Success

Throughout the interview, Roi emphasizes the importance of customer success and the role it plays in the growth of Uptick. He shares his philosophy on contracts and pricing, advocating for flexible and customer-centric approaches. Roi believes in letting customers go if they find a better software solution for their needs, as it is more important to maintain a positive brand reputation and customer satisfaction.

The Metrics that Matter: Driving Uptick's Success

Key Metrics for Uptick's Growth

When discussing the metrics that matter most to Uptick, Roi highlights the importance of pipeline generation and conversion rates. He believes that a healthy pipeline is a strong indicator of future success and allows for accurate forecasting. Roi also emphasizes the need for simplicity in compensation structures, aligning incentives with the company's goals and ensuring that sales teams are motivated to bring in the right customers.

Conclusion and Future Outlook: Uptick's Continued Success

Roi's Leadership and Vision for Uptick's Future

In conclusion, Roi's journey with Uptick provides valuable insights into the world of sales and scaling a business. His emphasis on learning by doing, hiring the right people, and focusing on customer success has been instrumental in Uptick's growth and success. As Uptick continues to expand and adapt to new challenges, Roi's leadership and commitment to excellence will undoubtedly drive the company forward.

Looking ahead, Roi envisions a future where Uptick continues to prioritize customer success and build strong relationships with its customers. He believes in the power of simplicity and alignment, and will continue to focus on the metrics that matter most to drive growth and revenue. With a strong team and a clear vision, Uptick is poised for continued success in the software industry.

Disclaimer: The views and opinions expressed in this article are those of the speaker and do not necessarily reflect the official policy or position of Uptick.

Subscribe to Ricky and Sean’s channel: https://substack.com/@saasytalkunfiltered


Ricky Sevta

Ricky is a seasoned leader with over two decades of experience in the B2B SaaS and construction technology industry. He has held senior leadership positions at Simpro, Schneider Electric, and other leading companies, consistently delivering exceptional results and guiding businesses to new heights of success.

Previous
Previous

SaaSy Talk Unfiltered: Shifting from Private Equity to becoming an operator

Next
Next

SaaSy Talk Unfiltered: The Power of Building a Strong Sales Team