Startup Life: Unscripted is a TNG Media newsletter, as part of The Nudge Group, where we feature candid conversations with startup operators about their career journeys and experiences. If you received this email as a forward, you can read all our past interviews and subscribe right here.

Behind the Scenes with Jason D’Silva: Steering Client Success Dashdot

Welcome back to Startup Life: Unscripted! On this episode, we're diving into the fascinating world of real estate tech with Jason D’Silva, Head of Client Success at Dashdot. He's breaking down his journey from e-commerce entrepreneur to driving client success at one of the most innovative startups in the property investment sector.

Key interview takeaways:

🔄 Career Pivot: Jason talks about the series of strategic shifts that took him from traditional real estate, through the world of telecommunications at Telstra, to the forefront of property investment technology with Dashdot.

🔧 Tools for Success: Jason shares the critical tools and strategies he employs to ensure client satisfaction and drive business growth within a startup environment.

🌟 Startups vs. Corporate Culture: Jason contrasts the fast-paced, meritocratic startup environment with his past corporate experiences, emphasising the opportunities to make a significant impact and the accelerated career growth available in the startup ecosystem.

🚀 Embracing Change and Innovation: Highlighting the importance of adaptability, Jason advises aspiring startup professionals to be prepared for the continuous learning and evolution required to thrive in a startup.

Hey Jason, it's a pleasure to have you here with us today. Your journey is quite a fascinating one, from leading teams in a corporate giant like Telstra to founding your own e-commerce businesses and now, playing a pivotal role at Dashdot. Can you walk us through your career adventure to date? 

My career has been an exciting and diverse one, filled with valuable experiences that have shaped me as a Client Success Leader. It all began at Telstra, where I started as a Retail Consultant whilst studying a double degree in Property and Commerce. Over the span of almost 4 years what started as a part-time job grew into several full-time leadership positions in Telstra’s retail and contact centre channels. 

Working at a large company like Telstra exposed me to the complexities of managing diverse teams, understanding the importance of clear communication, and honing my leadership and strategic decision-making skills. This corporate experience laid the foundation for my journey.

During my time at Telstra, I  also decided to embark on the entrepreneurial path by founding my three e-commerce businesses. This was a significant shift from the corporate world, and it taught me the true meaning of agility, adaptability, and resilience.

In the fast-paced and ever-changing landscape of e-commerce, I had to stay on top of market trends, customer preferences, and the latest technologies. This experience not only honed my business acumen but also helped me better understand the needs and pain points of clients, as I navigated through the challenges of running my own businesses.

Eventually, my journey led me to Dashdot, where I am currently the Head of Client Success. My previous experiences at Telstra and as an entrepreneur have uniquely contributed to my ability to understand and empathise with clients' perspectives.

From my corporate background, I bring the strategic thinking and team leadership skills necessary to drive successful client experiences. Meanwhile, my time as an entrepreneur has given me a deep appreciation for the importance of client satisfaction and the significance of building strong, long-lasting relationships.

In this role at Dashdot, I strive to leverage the best of both worlds, combining my corporate and entrepreneurial experiences to create innovative solutions that exceed our client's expectations. I firmly believe being client-focused and solution-oriented is the key to building successful partnerships and driving growth.

Overall, my career progression has been a series of valuable stepping stones that have contributed to my growth as a Client Success Leader. I'm grateful for each experience, as they have all played a unique role in shaping my skills, perspectives, and approach to serving our clients at Dashdot.

As the Head of Client Success at Dashdot, what does a typical day in your life look like? 

My days are usually dynamic and diverse, driven by the needs of our clients and the responsibilities of my role. While each day can be different, here's an outline of what a typical day in my life might look like

Setting up the day: I start my day by reviewing my schedule, prioritising tasks, and setting clear objectives for the day. I also catch up on any urgent emails or messages that may have come in overnight, ensuring I'm prepared for the day ahead.

Internal Team Collaboration: I work closely with our internal teams more specifically our Property, Sales, Marketing and Operations Teams. Collaborating with these teams is crucial to providing the best possible service to our clients.

Strategy and Planning: As a leader, I allocate time to strategize and plan for the future. This involves working on new initiatives to enhance client success, evaluating the effectiveness of existing processes, and identifying areas where we can improve.

Supporting the Team: There are two teams that sit under our Client Success Business Unit. The first is our Account Management Team who are the friendly warriors and main point of contact for our clients throughout their journey. The second is our Portfolio Strategist Team who work closely with our clients to understand their investment goals, risk tolerance, and financial objectives and create customised portfolio plans that align with these objectives. 

Both these teams have a senior team member who is responsible for the day-to-day running of the team. As the Head of Client Success, I primarily provide guidance and support to our Senior Account Manager and Senior Portfolio Strategist to ensure they have everything they need to set up their respective teams for success. This may include offering mentorship and coaching, resolving any challenges they face and working with them to achieve our trimester goals and objectives.

Industry Insights: Staying up-to-date with industry trends, best practices, and innovations is essential. I dedicate time each week to expand my knowledge and bring fresh ideas to our client success strategies.

End-of-Day Recap: Towards the end of the day, I take some time to review the progress made on various tasks, address any outstanding issues, and prepare for the following day's commitments.

Personal Growth and Well-being: It's crucial to maintain a healthy work-life balance. I make time for personal growth activities, such as reading, exercising, or spending quality time with family and friends.

Of course, unexpected situations and urgent matters can arise, which may require flexibility and adaptability. Being in a client-centric role means being ready to address client needs promptly and efficiently, even if it means adjusting my daily plan. Overall, my role as the Head of Client Success is challenging and rewarding, as it allows me to make a positive impact on our clients' experience with Dashdot and contribute to the company's success.

Working in both corporate and startup environments offers different kinds of challenges and rewards. How would you compare your experiences between the two, especially in terms of team dynamics, work culture, and pace?

Working in both corporate and startup environments has presented some interesting challenges and rewards. Here is a summary of my experience.

1. Team Dynamics

Corporate Environment: In a corporate setting like Telstra, team dynamics tend to be more structured and hierarchical. There are defined roles, established reporting lines, and clear chains of command

Startup Environment: At Dashdot we adopt a decentralised command model where our team is encouraged to make decisions within the scope of their roles and responsibilities. Furthermore being a smaller team, we often wear multiple hats and collaborate across departments to achieve business objectives.

2. Work Culture

Corporate Environment: At Telstra, the work culture prioritises stability, consistency, and adherence to established processes. Key decision-making often involved more layers of approval, leading to a slower pace in implementing changes.

Startup Environment: At Dashdot, we prioritise agility, innovation, and risk-taking. The emphasis is on rapid iteration, experimentation, and a willingness to adapt quickly.

3. Pace

Corporate Environment: Corporate environments can be relatively stable and predictable. While this can provide a sense of security, it might also mean slower decision-making processes and longer timelines for project execution.

Startup Environment: Startups are known for their fast-paced nature. Decisions are made swiftly, and team members must be adaptable to handle unexpected challenges.

Ultimately, both corporate and startup environments offer unique opportunities for personal and professional growth. The choice between the two often depends on an individual's preferred work style, risk tolerance, and career aspirations.

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With your entrepreneurial hat on, you've successfully founded three e-commerce businesses. What have been your key learnings from these ventures and how have they shaped your perspective when it comes to managing client success at Dashdot?

Starting three e-commerce businesses has given me invaluable insights and experiences that have greatly influenced my approach to managing client success at Dashdot. Here are some key learnings that have shaped my perspective:

1. Client-Centric Approach: One of the most significant lessons from my e-commerce businesses is the importance of putting the customer at the centre of everything we do. Understanding and empathising with the needs, pain points, and preferences of our clients is crucial for building strong and lasting relationships. At Dashdot we strive to instil a client-centric culture, ensuring that every team member understands the importance of meeting and exceeding client expectations.

2. Agility and Adaptability: The fast-paced and ever-changing world of e-commerce taught me the value of agility and adaptability. Market conditions, customer behaviour, and industry trends can shift rapidly, and businesses must be able to respond quickly. I bring this mindset to Dashdot, encouraging my team to be nimble and adaptive in addressing client needs and providing solutions that are relevant and effective.

3. Embracing Innovation: In the e-commerce space, embracing innovation and staying ahead of the curve is essential for survival and growth. I encourage a culture of innovation at Dashdot, where we constantly explore new ways to better serve our clients. This mindset ensures that we don't become complacent and always strive for continuous improvement.

4. Resilience and Perseverance: Entrepreneurship is not without its challenges, and there were times when I faced setbacks and obstacles. These experiences taught me the importance of resilience and perseverance. I bring this attitude to Dashdot, motivating my team to stay committed and overcome challenges together, especially during critical moments when clients may need our support the most.

6. Building Trust and Transparency: Trust is the foundation of any successful client relationship. I learned that transparency, open communication, and delivering on promises are essential in building and maintaining trust. At Dashdot, we prioritise transparent communication with our clients, ensuring they have a clear understanding of our processes, progress, and outcomes.

7. Listening and Learning from Clients: E-commerce businesses thrive when they actively listen to customer feedback and learn from it. At Dashdot, we encourage active listening and feedback loops with our clients. Understanding their perspectives and using their insights to improve our services demonstrates our commitment to their success.

Overall, my entrepreneurial experiences have shaped me into a leader who values innovation, client-centricity, and continuous improvement. These perspectives have been fundamental in my role as the Head of Client Success at Dashdot, as I aim to lead a team that is dedicated to delivering exceptional value to our clients and forging long-lasting partnerships based on trust, support, and mutual success.

Let's shift gears a little and talk about your personal career trajectory. You've traversed through different roles, industries, and even founded businesses. What prompted these transitions and how did you prepare for them? 

Great question! I’ve always had an interest in the property industry so after finishing high school and starting my university degree I immediately tried to get any property role I could. My interest in property stemmed from two areas.

The first one was my upbringing in Dubai. I was fascinated with the property development process that transformed a desert into one of the world's most iconic cities in just 20 years.

The second reason is a little silly in hindsight! When my family moved to Australia we moved house a few times so we were always working with Real Estate Agents and I was impressed by the suits, cars and their general lifestyle. From the outside looking in it seemed like real estate sales would be an amazing career path that would allow me to fund the lifestyle I was aiming for.

After doing both traditional real estate sales and property management roles I realised very quickly that this wasn’t the career path for me so I transitioned to Telstra to satisfy my interest in technology.

Working at Telstra gave me the flexibility to focus on other passion projects, one of which was e-commerce where a colleague and I worked on building and running a store in our off time that generated a six-figure net profit in just six months. This was an absolute game-changer and fundamentally shifted the way I thought about working and investing.

The second passion project I was working on during my time at Telstra was real estate investing. With the savings from Telstra, I decided to invest in property because I knew this would be a safe long-term investment.

I called a Business Development Manager I worked with at Ray White and he recommended looking at off-the-plan apartment developments in my local area and that was as far as my property investment due diligence went. I went to the fancy sales office of one of the projects and bought an apartment within my price point the next day.

I only realised how much of a mistake this was when it came time to settle. To name just a few of the challenges I faced:

• The property got undervalued by $50,000 so I had to make up the difference which thanks to the e-commerce profits I could

• The apartment was under the square metre criteria for the lender so I had to pay $4000 in legal fees to transfer to another apartment that was $40,000 more than the original apartment I purchased

• Finally to top it all off this was during the banking royal commission so my borrowing power had dropped significantly from what my broker told me when we got the property under contract so we had to go to a third-tier lender to get the loan across the line which was at significantly higher interest rates

The experience of buying this property demonstrated that I had no idea how to purchase investment-grade properties and filled me into absorbing every property investment book, podcast and webinar I could get my hands on so I don’t repeat the same mistake.

Alongside this experience, I was working on developing my leadership skills with Telstra and had stepped into an Assistant Store Manager role but I was still dead set on finding a role in the property industry because I knew I wanted to do something in this space I just didn’t know exactly what that was.

One day as I was scrolling through Seek I saw a role for a Client Account Manager at Dashdot and in the job description there was a video from Goose our CEO which really spoke to me.

I dug a bit deeper into Dashdot and saw that Goose and Gabi, our Co-Founders, had made the same property investment mistakes I did and this sparked their interest in looking to transform the way the world invests. From there I knew this was the company for me so I did everything I could to land the role and I haven’t looked back since.

Preparing for these career transitions was crucial to my success. Here is a summary of the behaviours I developed.

1. Entrepreneurial Drive: The desire for autonomy and the opportunity to create something of my own fueled my transition into entrepreneurship. I had a passion for innovation and a hunger to make a meaningful impact, which led me to start my own e-commerce business and work with Dashdot.

2. Seeking New Challenges: As I progressed in my corporate roles, I found myself seeking new challenges that would push me beyond my comfort zone. I wanted to explore different industries and expand my skill set, which motivated me to embrace new opportunities.

3. Skill Development: To prepare for each career transition, I focused on skill development. Whether it was leadership skills in my corporate roles, understanding the e-commerce environment, or building my property investment knowledge, I invested time and effort into acquiring the necessary skills to succeed in the new roles.

4. Continuous Adaptation: Embracing change and being adaptable were crucial in each transition. Whether shifting from a corporate environment to entrepreneurship or navigating diverse industries, the ability to adapt to new challenges and environments was key to my success.

5. Emotional Resilience: Career transitions can be emotionally challenging, especially when stepping into the unknown. Emotional resilience helped me overcome setbacks, stay focused on my goals, and maintain a positive outlook throughout my journey. I learned quite heavily on content from individuals like David Goggins and Jocko Willink to uplevel my knowledge in this area.

Thinking back to your own journey, what advice would you give to someone keen on making a shift from a corporate role to a startup? Are there certain skills or mindsets you believe are essential?

Making a shift from a corporate role to a startup can be both exhilarating and challenging. Having gone through this journey myself here are some of the skills and mindset shifts I would recommend your readers look into.

1. Embrace the Entrepreneurial Mindset: Startups require a different mindset than corporate environments. Embrace qualities like adaptability, risk-taking, resilience, and a willingness to learn from failures. Be prepared for ambiguity and uncertainty, as startups often operate in rapidly changing landscapes.

2. Passion and Purpose: Ensure that you are genuinely passionate about the startup's mission, product, or industry. Startups can sometimes demand intense dedication and long hours, so having a strong sense of purpose will fuel your drive during challenging times.

3. Be Open to Learning: In a startup, you may be required to wear multiple hats and take on tasks outside your comfort zone. Be open to learning new skills and taking on diverse responsibilities. Flexibility and a willingness to learn will be key to your success.

4. Build a Strong Support Network: Surround yourself with like-minded individuals who share your entrepreneurial spirit. Connect with mentors, other entrepreneurs, and support networks that can provide guidance and encouragement throughout your journey.

5. Be Patient and Persistent: Success in the startup space often takes time. Be patient, stay committed, and remain persistent, even in the face of setbacks or slow progress.

6. Celebrate Small Wins: Celebrate every milestone, no matter how small. Recognising progress and accomplishments, no matter how minor helps keep motivation and morale high.

Overall, transitioning from a corporate role to a startup requires a combination of courage, passion, and a growth mindset. It's a journey that can be incredibly rewarding, but it's essential to be well-prepared, adaptable and committed to the unique challenges and opportunities that come with the startup world.

Last question before we wrap up, being so deeply immersed in the startup world now, what aspects of it do you find most rewarding and what keeps you driven to excel each day?

So many! Here are just a few.

1. Impact and Purpose: One of the most rewarding aspects of the startup world is the opportunity to create a significant impact. At Dashdot our mission is to transform the way the world invests so knowing that the work I do can make a meaningful difference in our client’s lives motivates me to give my best each day.

2. Innovation and Creativity: At Dashdot we thrive on innovation and creativity. Being part of a dynamic environment where new ideas are constantly explored and implemented is incredibly inspiring. The freedom to experiment and think outside the box fosters a sense of excitement and pushes me to continuously seek innovative solutions.

3. Learning and Growth: Dashdot offers unparalleled opportunities for personal and professional growth. In my two and half years at Dashdot, I started as an Account Manager and from there was promoted to a Client Success Team Lead and now the Head of Client Success.

In a traditional corporate environment, this trajectory would have likely taken double the time to achieve if not longer. Each day presents unique challenges that require me to adapt, learn, and develop new skills. This continuous learning process keeps me engaged and driven to excel in my role.

4. Building Relationships: At Dashdot, relationship-building is fundamental. I find immense satisfaction in forging strong connections with clients, team members, partners, and other stakeholders. The collaborative nature of our business fosters a sense of camaraderie and shared purpose, creating a positive and supportive work environment.

5. Sense of Ownership: The work I do at Dashdot provides a sense of ownership and autonomy that is truly fulfilling. Having the opportunity to contribute directly to the company's success and see the results of my efforts firsthand is incredibly rewarding.

6. Fast-Paced Environment: The fast-paced nature of startups keeps me on my toes and prevents monotony. Every day brings new challenges and opportunities, making the work environment exciting and dynamic.

7. Making a Vision a Reality: Witnessing a vision or idea evolve into a tangible reality is a rewarding experience. Starting with a vision, and the journey of transforming that vision into a viable product or service is both fulfilling and motivating.

The startup world offers a unique blend of purpose-driven work, creative freedom, and continuous growth opportunities. The excitement of being at the forefront of innovation, creating meaningful impact, and collaborating with a vibrant community of individuals keeps me driven to excel each day. It's a journey filled with challenges and rewards, and the ability to make a positive difference in the world fuels my passion and commitment.

From the Startup Life team

And that's a wrap! We hope you've enjoyed this edition as much as we loved putting it together. Stay curious, keep learning, and above all, enjoy the rollercoaster ride that is Startup Life. Catch you in the next one! 👋 Not subscribed yet? Do it here and don't miss out! Subscribe Now.

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