One on One Interviews

I first spoke with Rich Rao almost eight years ago when he was Director of Worldwide Sales and Operations for Google. And earlier this week I caught up with him for a LinkedIn Live conversation for the first time since then, but now Rich is Vice President, Small Business at Facebook.

Rich shared with me how Facebook is working to help small businesses transition to doing more business online, the role AI can play in helping these businesses more efficiently and effectively connect with potential new customers, and how they are incorporating Instagram and WhatsApp into an integrated approach to community building.

I known the HubSpot co-founders, Brian Halligan and Dharmesh Shah, since July of 2006. And from a cheap row seat I’ve watched them take the company public, and grow it from just them to close to 4000 employees. And even though I think I know the story pretty well, and have spoken with both of them throughout the years for this series – the last time being four years ago with Dharmesh at the companies Inbound conference – I always learn something new about what they’ve done and how they’ve done it. That continued earlier this week when I had a LinkedIn Live conversation with Dharmesh.

Now, Dharmesh doesn’t do a ton of these, so I was really glad he joined me and shared a number of things during our discussion. Below is an edited transcript of a portion of our conversation, where he talks about the early days of building the company, why the partnership with Brian has been so long lasting and successful, and why a guy who describes himself as an introverted tech geek decided to write a culture code that has turned into, as he puts it, one of the greatest contributions to the company.

We’re full-throttle into the holiday shopping season having blown past Black Friday and Cyber Monday – which by the way broke the single day online US shopping record with $10.84B spent, according to Adobe Analytics.

But now that we’re closing in on the big day, and every minute counts towards making sure what you order makes it to where it needs to go in time for the big day, shoppers are turning to Old Faithful, aka Amazon.com, to make sure the magic happens. But a recent report on CNBC had me wondering if Amazon is ready. The title of the segment was “Amazon pushes holiday shoppers to pick up packages at stores amid potential delivery crunch.”

But doesn’t that go against the main reason we all turn to Amazon in the first place? The convenience of having our stuff sent to our homes is what got us hooked, and the belief that we’ll get that stuff when we need, is what kept us hooked. But if that’s not the case, if we have to go and pick it up to make sure we get it, does that make Amazon less attractive to turn to? Me and my Watching Amazon co-host John “ColderIce” Lawson had to toss it around a bit.

Recently I spoke with Keala Gaines, VP of Global Payment Services for eBay, to learn more about the impact modern payment technology is having on the customer experience, how having the payment tech on certain device types can help increase conversion opportunities, and how using the latest technology can also make things run more efficiently.

Earlier this week I spoke with Clark Twiddy, president Twiddy and Company, to hear how they used the SAS data analytics platform and Clark’s military background with intelligence to bring data science to his family-owned small business. And how that helped the company to “digitize their southern hospitality” and create new opportunities even in the heart of a pandemic that is crushing the travel and leisure industry at large.

I’ve known Mike Volpe for well over a decade, going back to his days as HubSpot’s first chief marketing officer. And I’ve spoken with him a few times over the years for the series, the last time being when he became the new CEO of Lola.com a little over two years ago. As a refresher, Lola.com is focused on making business travel easier for the travel manager and the traveler.

Being that business, it’s not surprising that the pandemic has had a major negative impact on Lola. But even that would be an understatement as the company lost 97% of its revenue when travel basically came to a screeching halt overnight at the beginning of the Covid-19 shutdown. 97%!

Knowing the industry that he was in, I remember checking in on Mike at the onset of the pandemic via email. He told me that I should check back in a couple of months because they were working on a plan. And roughly five months later, Lola just announced a new service offering called Lola Spend, that helps companies to track expenses and manage spending. And the new offering was actually in part a collaborative effort from the same Lola customers who stopped traveling.

The folks at Adobe recently put out their holiday season shopping forecast, based on one trillion visits to US retail websites. Yes, you read that right – one TRILLION visits to retail websites in the country. And some of the key predictions include:

• Online holiday spend will surpass $189B (up 33% YoY)

• Black Fri: $10.3B (39% YoY); Cyber Mon $12.7B (35% YoY)

• 42% of all online shopping done from smartphones (up 55%)

• Small retailers ($10-$50M): +107% daily revenue boost for season

• 26% of consumers say knowing the election outcome will impact their holiday spend*

These are just a few of the interesting data points in the forecast. And to get a little more insight into the numbers I spoke with Vivek Pandya, Adobe’s Senior Digital Insights Manager.

With the pandemic impacting so many aspects of our daily lives – both personally and professionally – I was curious to find out how it is effecting how things in the venture capital space. And last week I had the opportunity to speak with Scott Beechuk, Partner at Norwest Venture Partners. Norwest is a leading venture and growth equity investment firm managing more than $9.5 billion in capital, and Scott focuses on early- to late-stage investment opportunities in enterprise SaaS with a focus on companies building business applications taking advantage of human-assisted AI, advanced behavioral analytics, client-agnostic platforms and industry-specific solutions.

Scott shared how his experience as an entrepreneur and later at Salesforce as SVP in product management has helped shape his approach to being a VC, and how COVID-19 has impacted how he operates.

Late last month Salesforce introduced Digital 360, combining their Marketing, Commerce, and Experience Clouds with some new components to help companies accelerate their digital transformation efforts with respect to customer engagement. And earlier this week I had the pleasure of having a LinkedIn Live conversation with Adam Blitzer, EVP & GM, Digital for Salesforce, to talk about how the coronavirus is affecting digital transformation efforts and causing foundational changes to companies will need to engage customers and prospects long after the pandemic is over.

Throughout the most of this year during the pandemic I’ve had the opportunity to speak with executives at a number of technology companies serving the small business community. And while there are a number of themes that have recurred with many vendors and across the months we’ve been dealing with COVID-19, the ones that have resonated with me have been the descriptions for small businesses I’ve heard over and over again: innovative, creative, resilient and inspired. And during a recent conversation with Melissa Schneider, GoDaddy’s VP Global Marketing Operations & Product Marketing, she went even further in detailing a couple of real life examples of just how resilient and inspired small businesses have been in order to survive and succeed in the midst of the coronavirus.