34. How do you build an organisation to compete with Google?

In this episode we are joined by Omid Ashtari, ex-COO of Streebees and President of Citymapper.

3/14/20241 min read

We chat about the following with Omid:

  • How do you think about organisational structure?

  • How proactive should you be in anticipating organisational challenges?

  • What is the highest impact communication challenge you helped resolve?

  • How do you prevent drift from the customer as the company scales?





I have two decades of experience in tech and worked in sales, business development and strategy roles for Google across the Dublin, London and San Francisco office during his 7 years there. As the first international employee, I set up Foursquare in Europe as Managing Director. I subsequently joined Citymapper for 6 years as President running the non-engineering side of the business. I then joined Streetbees as COO running operations, international expansion, finance and legal. Throughout my career I have raised north of 100 million dollars of funding for businesses I have worked for.

I am an angel investor in more than 45 businesses and advise many of them in all manner of things including strategy, operations, business development, fundraises etc. I am also part of the Mayor of London's Business Advisory Board, and a Mentor at Seedcamp and Entrepreneur First.

I am also an aspiring writer for my blogs startuppragmatism.blog and thefullspectrum.blog.

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  • Personal growth and evolution over 13 years. 0:05

    • Brandon reflects on his past solo travels and how they relate to his current life.

    • Brandon M reflects on his past self-absorption and lack of empathy, now prioritizing supporting others' success and empathy in personal and professional life.

    • Brandon M recounts a 2011 incident where he carried a biscuit tin full of Canadian coins and sat next to a homeless person, now recognizing the importance of empathy and caring for others.

  • Organizational structure and skills for a business. 4:09

    • Bethany: People often create an org structure that prioritizes making their existing team happy, rather than starting fresh and building a structure that works for the business.

    • Brandon M: Bethany suggests starting with a blank slate and building an org structure that works for the business, rather than trying to fit existing team members into a pre-existing structure.

    • Bethany and Brandon M discuss the importance of defining the skills needed for a business to succeed, rather than simply morphing structures around people.

    • They agree that it's better to have a flexible approach to organizational structure, recognizing that roles may evolve as the business grows and changes.

  • Organizational design and hiring for a scaling startup. 9:57

    • Brandon M. faced pushback on hiring 2 product marketing managers, but believes it was necessary for success in both self-serve subscribers and enterprise sales.

    • Brandon M. emphasizes the importance of clear go-to-market strategy and collaboration between product marketing manager and go-to-market manager.

    • Bethany identifies the need for a "thinker" in early-stage businesses to analyze and gather information, which is perceived as a luxury role but essential for product market fit and growth.

    • Bethany highlights the importance of having a thinker and a strategic salesperson in a scaling organization, as they provide valuable insights and help navigate challenges.

    • Bethany identifies signs of organizational design issues, including unhappiness, confusion, and a lack of managers or promotional opportunities, which can lead to restructuring.

  • Organizational structure and scaling. 16:27

    • Omid Ashtari discusses the importance of adapting organizational structure to the scale of the problem being solved, as the number of employees grows.

    • Ashtari highlights the challenges that arise when an organization expands, such as natural breaking points and lines of communication, and the need to adjust operational systems accordingly.

  • Communication and decision-making challenges in scaling startups. 18:37

    • Omid Ashtari explains how companies can proactively address problems by embracing chaos and redesigning systems after hiring new employees.

    • Omid Ashtari highlights the importance of clear communication and decision-making processes in startups, particularly in scaling businesses.

    • He shares an example of a company experiencing success bias, where they lose humility and become less secure, leading to bottlenecks in decision-making and communication.

  • Product-market fit and organizational structure for startups. 22:39

    • Omid Ashtari highlights the importance of addressing user complaints and recalibrating employees' understanding of the product's performance in different cities.

    • Citymapper encourages engineers and employees to travel to different cities for exploratory trips to better understand user needs and improve the product.

    • Omid Ashtari discusses the importance of understanding customer needs and maintaining product-market fit in scaling startups.

  • Hiring for various roles in a business, focusing on cognitive ability and adaptability. 26:49

    • Omid Ashtari discusses the importance of hiring the right person for the job, particularly in scaling problems, where high roller related knowledge is crucial.

    • Ashtari highlights the challenge of figuring out the business model for a problem like city mapper, where role related knowledge is less important than adaptability to the organization's synchronous ease.

    • Omid Ashtari emphasizes the importance of hiring people with high cognitive flexibility and entrepreneurial mindset for a specific business unit within a company.

    • He describes a cross-functional team structure where team members sit in different rooms and communicate ad hoc to solve problems quickly, with a central table for impromptu meetings.

  • Scaling a transportation app company. 32:26

    • Omid Ashtari emphasizes the importance of adapting to changing business needs by creating separate units with different operating systems to address specific problems.

    • In Citymapper's case, the main focus was on retaining organic growth in London, with a myopic focus on product innovation and weekly updates to address user feedback.

    • Omid Ashtari describes the challenges of scaling a transport app, including competing with Google Maps and Apple Maps, and the need for a sustainable business model.

    • Ashtari highlights the importance of resilience and entrepreneurial spirit in overcoming these challenges, and the need for tooling to enable non-engineers to launch cities.

  • Entrepreneurship, product market fit, and organizational design. 37:48

    • Omid Ashtari emphasizes the importance of asking questions and reorganizing as needed in the face of uncertainty.

    • Citymapper's team has adapted to changing needs by reassigning personnel and launching new initiatives like smart ride, a cab-based ride-sharing service.

    • Omid Ashtari emphasizes the importance of being "confidently insecure" as an entrepreneur, constantly reassessing and adapting to changing circumstances.

    • Bethany agrees, highlighting the need to be emotionally intelligent, flexible, and humble in the face of uncertainty and criticism.