EPISODE 160: Marketer of the Month Podcast with Sukhinder Singh Cassidy

Hey there! Welcome to the Marketer Of The Month blog!

We recently interviewed Sukhinder Singh Cassidy for our monthly podcast – ‘Marketer of the Month’! We had some amazing insightful conversations with Sukhinder and here’s what we discussed about-

1. Entrepreneurial insights: Emphasizing continual decision-making over a single perfect choice for success.

2. Tough entrepreneurial decisions: Managing cash, halting businesses, and staffing adjustments for financial sustainability.

3. Business development strategy: Juggling multiple opportunities to refine negotiation skills and foster business growth.

4. Negotiating prowess: Small businesses setting firm positions in negotiations with larger corporations.

5. Efficiency via cloud technology: Streamlining tasks, like accounting, to save costs and time for small businesses.

6. AI’s role in financial management: Predicting AI’s broader integration beyond generative AI for enhanced efficiency.

About our host:

Dr. Saksham Sharda is the Chief Information Officer at Outgrow.co. He specializes in data collection, analysis, filtering, and transfer by means of widgets and applets. Interactive, cultural, and trending widgets designed by him have been featured on TrendHunter, Alibaba, ProductHunt, New York Marketing Association, FactoryBerlin, Digimarcon Silicon Valley, and at The European Affiliate Summit.

About our guest:

Sukhinder Singh Cassidy, a tech leader and entrepreneur, served as StubHub’s president. She’s held key roles at Google, Amazon, News Corp, Yodlee, and Polyvore. In 2011, she founded JOYUS, a video shopping platform for women, leading as CEO and Chairman until 2017. She’s also the Founder of theBoardlist, advocating for boardroom diversity.

Cash, Cuts, and Comebacks: Xero’s CEO Sukhinder Singh Cassidy on the Tough Choices that Lead to Triumph

The Intro!

Saksham Sharda: Hi, everyone. Welcome to another episode of Outgrow’s Marketer of the Month. I’m your host, Dr. Saksham Sharda, and I’m the creative director at Outgrow. co. And for this month we are going to interview Sukhinder Singh Cassidy, who is the CEO at Xero.

Sukhinder Singh Cassidy: Great to be here. Thank you.

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The Rapid Fire Round!

Saksham Sharda: Okay, the first one is, at what age do you want to retire?

Sukhinder Singh Cassidy: 75.

Saksham Sharda: How long does it take you to get ready in the morning?

Sukhinder Singh Cassidy: Five minutes.

Saksham Sharda: Most embarrassing moment of your life?

Sukhinder Singh Cassidy: When I introduced myself, not as the CEO on my first results, call it zero.

Saksham Sharda: Favorite color?

Sukhinder Singh Cassidy: Blue. Maybe not. I don’t have a favorite. I’m trying to think of my favorite color.

Saksham Sharda: That was a good reaction to your favorite color.

Sukhinder Singh Cassidy: Blue, purple, green, pink.

Saksham Sharda: What time of day are you most inspired?

Sukhinder Singh Cassidy: Maybe mornings.

Saksham Sharda: How many hours of sleep can you survive on?

Sukhinder Singh Cassidy: Three.

Saksham Sharda: Fill in the blank. An upcoming remote work trend is ___.

Sukhinder Singh Cassidy: Upcoming remote work trend pass. I’ll come back to it.

Saksham Sharda: The city in which the best kiss of your life happened.

Sukhinder Singh Cassidy: San Francisco. My husband would be insulted if I said anything else.

Saksham Sharda: Pick one. Mark Zuckerberg or Elon Musk?

Sukhinder Singh Cassidy: Neither.

Saksham Sarda: Why the split question? So I’m going to take that as a pass—the biggest mistake of your career?

Sukhinder Singh Cassidy: Oh. Do I have to pick one? Then I’ll go back and pick Mark Zuckerberg.

Saksham Sharda: Pick one. Mark Zuckerberg or Elon.

Sukhinder Singh Cassidy: Musk. Mark Zuckerberg. Okay.

Saksham Sharda: The biggest mistake of your career?

Sukhinder Singh Cassidy: Going places where my strengths weren’t valued and my values weren’t shared.

Saksham Sharda: How do you relax?

Sukhinder Singh Cassidy: Tennis and shopping.

Saksham Sharda: How many cups of coffee do you drink per day?

Sukhinder Singh Cassidy: Like three in the morning. And then I switch to something else.

Saksham Sharda: A habit of yours that you dislike?

Sukhinder Singh Cassidy: Interrupting other people.

Saksham Sharda: The most valuable skill you’ve learned in life.

Sukhinder Singh Cassidy: It all works out as it’s meant to.

Saksham Sharda: Your favorite Netflix show.

Sukhinder Singh Cassidy: Never have I ever.

Saksham Sharda: The last movie that had a good impression on you.

Sukhinder Singh Cassidy: Creed 3.

Saksham Sharda: The last song you’ve been listening to.

Sukhinder Singh Cassidy: My all-time favorite song is Walk on Water.

The Big Questions!

Saksham Sharda: Alright, so that’s the end of the rapid-fire round. Okay. We’re going to go onto the longer questions now, which you can answer with as much ease and time as you like.

Saksham Sharda: Okay. The first one is, so to a new entrepreneur who’s starting their journey, what tips will you give them for sustaining their entrepreneurial voyage?

Sukhinder Singh Cassidy:  So I think the most important thing to sustain your entrepreneurial voyage is remembering two things. Number one, it’s never a single choice. Often the pressure on entrepreneurs is like you have to choose once, and you have to be perfect. But being an entrepreneur is a constant journey of choices. You’re going to have 1000- 100,000 choices between you and success. So take the pressure off the first choice. To just get started. That’s my first one. My second one is probably to pay attention to who you want in your boat. Often entrepreneurs feel pretty lonely because you’re doing it alone, but even one person to share the journey with makes a difference. That could be if you can’t afford someone. It could be just who you talk to as sort of your professional priest. If you’re going to make your first hire, make it one. Who, as I said, has complementary strengths to yours but shares your values.

Saksham Sharda: And what are some of the tough decisions you’ve had to make in your journey?

Sukhinder Singh Cassidy: I think the toughest decisions for any entrepreneur are the decisions around how to manage your cash. You know, often that makes painful decisions around, you know, businesses to stop even if you believe they’re great, they may not be great for now. You have to constrain your focus. Sometimes it makes really hard decisions, you know, just to make your cash go longer. So often, those are the toughest decisions, what not to do or what to stop doing because, as an entrepreneur, you can see the value in, you know, everything you’re trying and the value in all the people you know you might have assembled around yourself.

Saksham Sharda: What is your take on building business development skills and, ultimately, strategies?

Sukhinder Singh Cassidy: Business development skills? Very simple. Business development is all about having multiple threads going at once. People think that business development is about making one deal work. No, you want to drive eight or nine different opportunities like a classic funnel to the end and then narrow your choice set at a minimum. It’ll make you a better negotiator, but often it will surprise you what you learn on the journey of opening up, you know, nine or 10 different threads with different companies before deciding who you ultimately want to work with. 

Saksham Sharda: So, could you share a memorable example of a business development strategy that yielded significant results of growth for a company you’ve worked with?

Sukhinder Singh Cassidy: Sure. I’m going to give you a different example, which is that, as a small business, you often think you can’t negotiate. And I remember when I was early on at Yodlee and I was our co-founder and head of business development, we were negotiating with the biggest banks in the world like a city group or other things. And I remember everyone thought we couldn’t negotiate with them, that we just had to take their terms. And at some point, you know, we figured out what our walkaway positions were and they would come to the table and I just said, no. And you think that if you’re a small business, you can’t negotiate against a big business. If they wanna do business with you, you can also set your positions and you can negotiate with a bigger company. So it’s okay to say no.

Saksham Sharda: So let’s shift to cloud technology. How can small businesses use cloud technology to enhance their business unit?

Sukhinder Singh Cassidy:  Well, I think the number one way to use cloud technology is to get rid of tasks that are time-consuming and paper-driven. Accounting is a key example of that. So often when you go to the cloud, two things happen. Number one, you can save time and resources by taking offline tasks and putting them online. And the other thing about cloud accounting that is important or cloud in general is the services are priced for what you use. And so often your cost of entering, you know, any new cloud technology is pretty low.

Saksham Sharda: And so what do you think of the enormous competition between cloud service, and cloud-based services that we’re seeing in the market today?

Sukhinder Singh Cassidy: Well, I think that benefits small businesses, right? Like I said, remember that earlier tip like go, you know, look at three or four choices before you make your decision. You should be able to take advantage of that enormous competition for either better services or better pricing.

Saksham Sharda: And what tips would you have for cloud-based service providers at this point?

Sukhinder Singh Cassidy: Focus on your customer.

Saksham Sharda: Alright, so which current digital transformations that are going on do you think are going to change the future of work itself?

Sukhinder Singh Cassidy: Of course, I think that small businesses, bringing all of their cash management online are gonna change the world because small businesses power the world. 99% of all businesses in almost any given GDP or economy are small businesses. So of course I believe that managing all your finances online is game-changing.

Saksham Sharda:  And what would be the future of managing finances online? What are some of the exciting things you would say?

Sukhinder Singh Cassidy: Do I hate to say ai? Of course, I’m going to say, I mean we are at zero. I think it’s important to remember it’s not just generative AI, it’s AI. Everybody is very focused on generative AI, but remember companies like Zero have been using AI to automate tasks for years. So AI I think will continue to be a trend, but not just the nifty new stuff. The stuff that companies have been doing for a long time to save manual processing time.

Saksham Sharda:  Could you repeat?

Sukhinder Singh Cassidy: This I say includes the AI the companies have been doing for a long time to keep automating manual tasks.

Saksham Sharda: Okay. So what are three things that a small business owner should be doing that will help them save time, and money and enable them to support their customers more?

Sukhinder Singh Cassidy:  Okay, number one, manage your cash very actively. A lot of small businesses think they’re profitable, but their cash books don’t reflect it because they’re not good at invoicing and collecting money. Like when small businesses are trying to stay alive, the number one thing you can do is maximize your cash and manage it, right? Like, get your invoices out faster. Utilize tools like Xero to manage it and close that gap between invoicing and payments, right? Consider implementing a small business invoice template to streamline the process even further. That is like cash in is the lifeblood of a small business. It’s cash management. That’s sort of like number one. Number two, and it’s obvious you know your customer, right? I mean, small businesses survive because they offer a valuable service to their customers. So, you know, I’m always like, just understand what your customers need from you and just completely focus on why they love you and do more of that.

Saksham Sharda:  And is there another one?

Sukhinder Singh Cassidy:  I think as a small business you have to learn what to say no to. By the way, that’s the same problem that big businesses have. You know, focus, focus, focus. I understand all entrepreneurs, myself included, are optimists and we live for all the future things we can do. But when you’re a small business, you have to decide what to do today. Quite frankly, that’s not that different from a big business to add the most value.

Saksham Sharda: Do you have a story about a particular small business that you’re pretty excited about?

Sukhinder Singh Cassidy: The board list, I’m the founder of a small talent startup that we started eight years ago. We are the classic small business. We’ve raised only a series seed and try to be mission-driven in terms of opening up opportunities for all the world’s diverse leaders to make their way to boards and help them perform better. We’ve stayed very focused on the niche of just solving board diversity to drive better outcomes. And of course, it’s the thing I’m passionate about because I’m passionate about making sure that boards perform better for all their constituents. And, we know that diverse talent helps solve that.

Saksham Sharda:  Okay, so the last question for you is like a personal kind. What would you be doing in your life, if not this right now?

Sukhinder Singh Cassidy: What would I be doing with hanging out with my kids more, playing more tennis? But to be honest, I’d probably drive them both crazy if I wasn’t working.

Let’s Conclude!

Saksham Sharda: Thanks, everyone for joining us for this month’s episode of Outgrow’s Marketer of the Month. That was Sukhinder Singh Cassidy, who is the CEO at Xero.

Sukhinder Singh Cassidy: Great to be here. Thank you.

Saksham Sharda: Check out the website for more details and we’ll see you once again next month with another marketer of the month.