SaaSy Talk S01.05: Building a Remote-First Unicorn Company: Challenges and Successes

09/14/23 • 35 min

About The Guest(s):

Co-Founder and Co-CEO Alina Vandenberghe created Chili Piper in 2016, the conversion platform for B2B sales, marketing, and implementation teams. With 45,000+ customers like Spotify, Airbnb, Gong, and Shopify, Chili Piper automates scheduling, lead qualification, and routing throughout all stages of the funnel.

The born entrepreneur started her first company before high school before she even knew what entrepreneurism was. After building mobile products loved by millions — and that were keynoted by Steve Jobs on stage — Alina decided to take her product management talents to B2B software solutions

Summary:

Alina Vandenberghe, CEO and co-founder of Chili Piper, shares her journey from Romania to the US and her passion for entrepreneurship. She discusses the challenges of working in corporate America and the freedom she found in building her own company. Alina also talks about the benefits and challenges of working with her husband as a co-founder and the importance of managing conflict in a relationship. She explains why Chili Piper decided to be a remote-first company and how they maintain a vibrant culture despite being geographically dispersed. Alina also provides insights into their hiring process for remote workers and the key characteristics they look for in candidates. She discusses the importance of onboarding and the need for self-accountability in a remote work environment. Alina shares her excitement for the future of Chili Piper and the challenges of scaling the business. She emphasizes the importance of being a problem solver and the joy she finds in building things.

Key Takeaways:

Alina's drive for independence and freedom led her to pursue entrepreneurship and build her own company.
Working with a spouse can be rewarding if there is trust, respect, and effective conflict management in both personal and professional life.
Remote work offers flexibility and freedom, but it requires self-discipline and the ability to manage loneliness.
Hiring remote workers requires finding individuals who are self-sufficient, have good work habits, and can thrive in a remote work environment.
Onboarding is crucial for remote workers to ensure they understand the company's values, products, and remote work expectations.

Quotes:

"The fact that it's hard and complicated, that's what excites me the most."
"I always wanted to be the CEO of a company ever since I was a child."
"We recommend that (remote workers) work out of an office, a shared office, a co-working space with other people."
"As long as the values that are important to us are instilled and we are supporting their growth... then I think they're going to be okay."
"Every stage of the company is really hard because you've not been exposed to it before... it's an ever-evolving skill set."

Chapters:

(0:00:30) Alina's desire to come to the US for more opportunities

(0:02:35) Alina's dissatisfaction with corporate America and desire for independence

(0:03:44) Alina and her husband's successful working relationship at Chili Piper.

(0:08:19) Characteristics sought in remote workers: self-sufficiency and self-accountability.

(0:15:35) Moments of realization that the business was taking off

(0:18:44) Transitioning from founder-led sales to external leadership

(0:21:19) Work life integration vs work life balance

(0:25:52) Balancing CEO responsibilities and collaborating with the board

(0:32:39) Excitement about growing Chili Piper and facing new challenges

(0:33:57) Quick Fire-Round

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About The Guest(s):

Summary:

Key Takeaways:

Alina's drive for independence and freedom led her to pursue entrepreneurship and build her own company.
Working with a spouse can be rewarding if there is trust, respect, and effective conflict management in both personal and professional life.
Remote work offers flexibility and freedom, but it requires self-discipline and the ability to manage loneliness.
Hiring remote workers requires finding individuals who are self-sufficient, have good work habits, and can thrive in a remote work environment.
Onboarding is crucial for remote workers to ensure they understand the company's values, products, and remote work expectations.

Quotes:

"The fact that it's hard and complicated, that's what excites me the most."
"I always wanted to be the CEO of a company ever since I was a child."
"We recommend that (remote workers) work out of an office, a shared office, a co-working space with other people."
"As long as the values that are important to us are instilled and we are supporting their growth... then I think they're going to be okay."
"Every stage of the company is really hard because you've not been exposed to it before... it's an ever-evolving skill set."

Chapters:

(0:00:30) Alina's desire to come to the US for more opportunities

(0:02:35) Alina's dissatisfaction with corporate America and desire for independence

(0:03:44) Alina and her husband's successful working relationship at Chili Piper.

(0:08:19) Characteristics sought in remote workers: self-sufficiency and self-accountability.

(0:15:35) Moments of realization that the business was taking off

(0:18:44) Transitioning from founder-led sales to external leadership

(0:21:19) Work life integration vs work life balance

(0:25:52) Balancing CEO responsibilities and collaborating with the board

(0:32:39) Excitement about growing Chili Piper and facing new challenges

(0:33:57) Quick Fire-Round

Subscribe on Spotify:

SaaSy Talk Unfiltered | Podcast on Spotify

Subscribe on YouTube:

SAASY TALK UNFILTERED - YouTube

Subscribe on Linkedin:

https://www.linkedin.com/company/saasy-talk-unfiltered

Subscribe to our Newsletter:

SaaSyTalkUnfiltered | Substack

Visit our Website:

SaaSy Talk Unfiltered (transistor.fm)

Follow Ricky Sevta on Linkedin:

Ricky Sevta | LinkedIn

Follow Sean Diljore on Linkedin:

Previous Episode

SaaSy Talk S01.04: Chris Orlob Discusses Sales, Hiring, and Scaling at Gong and P Club

About The Guest(s):

Chris Orlob is the CEO of pclub.io - the #1 online learning and skills platform for revenue professionals. Prior to that, he helped grow Gong from $200k to $200M ARR and a $7.2 billion valuation within 5 years.

Summary:

Chris shares his journey into sales, starting with selling golf balls as a child and later realizing the potential for a lucrative career in sales. He joined Gong, a startup in its early stages, and played a key role in its growth. Chris emphasizes the importance of a clear hiring profile and a repeatable sales process. He also discusses the impact of AI on sales and the future of the industry. Chris advises founders to invest in marketing and build an audience of superfans. He also highlights the need for business acumen and intellectual horsepower in sales reps.

Key Takeaways:

Chris emphasizes the importance of hiring people with business acumen and raw intellectual horsepower.
Investing in marketing and building an audience of superfans is crucial for success.
The future of sales may involve AI-driven skill assessments and AI role plays.
The first comp plan for early hires should be focused on new customer acquisition and be generous with accelerators.

Quotes:

"Business acumen is probably the most underrated body of knowledge when it comes to sales success."
"If you don't piss somebody off by noon each day, you're not marketing your business hard enough."
"Most startups are trying to acquire new customers, so you should orient the commission payout to be almost exclusively on new customer acquisition."
"Be generous when people perform, but be stingy if they don't."

Chapters:

(00:00) Introduction and discussion about how Chris got into sales

(04:10) Gong was a small company with $178,000 ARR when Chris joined

(10:41) Gong cracked the code by creating a playbook for success

(14:41) Developing hiring profiles for salespeople.

(21:06) Hiring for ambiguity is still a challenge for P Club.

(25:15) Need to hire builders as the company scales

(26:37) Overview of P Club and its vision

(31:37) Future of sales and AI

(35:20) Biggest mistake founders make when scaling

(46:41) Quick Fire-Round

Subscribe on Spotify:

SaaSy Talk Unfiltered | Podcast on Spotify

Subscribe on YouTube:

SAASY TALK UNFILTERED - YouTube

Subscribe on Linkedin:

https://www.linkedin.com/company/saasy-talk-unfiltered

Subscribe to our Newsletter:

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Visit our Website:

SaaSy Talk Unfiltered (transistor.fm)

Follow Ricky Sevta on Linkedin:

Ricky Sevta | LinkedIn

Follow Sean Diljore on Linkedin:

Sean Diljore | LinkedIn

Next Episode

SaaSy Talk S01.06: Building a Unicorn startup requires aligning culture, hiring the right people, and focusing on key metrics

About The Guest(s):

Ashik Ahmed is the co-founder, ex-CEO of Deputy, now a board member of Deputy, a global workforce management platform for employee scheduling, timesheets and communication.

Summary:

Ashik Ahmed, co-founder of Deputy, shares his journey of starting the workforce management software company and the lessons he has learned along the way. He emphasises the importance of finding the right fit for executives and the need to align their values with the company's mission. Ashik also discusses the challenges of scaling a business and the importance of maintaining a strong company culture. He highlights the need for founders to prioritise their mental well-being and family life, as they are the most important assets for the business.

Key Takeaways:

Executives should be aligned with the company's values and mission to ensure success.
Hiring the right people is crucial, as the wrong fit can lead to negative outcomes.
Founders should prioritise their mental well-being and family life to maintain a healthy work-life balance.
Operational excellence is key to success, and companies should strive for continuous improvement.
Building a strong company culture is essential for long-term success.

Quotes:

"Just because they have done very well, it's not that they will do very well over here." - Ashik Ahmed
"Failure is not an option." - Ashik Ahmed
"Culture is the collective behaviour of everybody that works in the company." - Ashik Ahmed
"Don't victimise yourself. You are one of the most fortunate people in the world." - Ashik Ahmed

Chapters:

(00:41) Ashik's journey and how he co-founded Deputy

(02:41) Challenges and doubts faced in the early years

(05:00) Failure in outbound sales and the win with the Xero partnership

(09:27) Learning from mistakes and not giving up

(12:00) Challenges of maintaining culture as a company scales

(15:00) Importance of hiring the right executives

(21:46) Differentiating between valuable advice and "bullshit"

(25:10) The importance of different focuses at different stages of a company

(27:06) Balancing time with team and board as CEO.

(33:39) Quick fire-round

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