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Cache Flow Podcast

E45: Competing with Giants: HelpSpot’s Challenges and Strategies in Help Desk Software

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In this podcast episode, host Brian Dainis engages in a captivating conversation with Ian Landsman, the Founder of HelpSpot, a key player in the competitive world of help desk software. They delve into HelpSpot’s unique position in this market, the challenges of competing with industry giants, and the delicate balance between customer customization and product development in the realm of SaaS. The episode explores the power of cold outreach, the significance of IP addresses in consulting, and emerging trends in tech, including AI’s potential impact on customer service jobs and chatbot services. Tech enthusiasts and entrepreneurs will find this discussion a fascinating dive into the tech industry’s intricacies and the future of customer support.

Ian Landsman is the Founder and 100% Owner of UserScape, Inc., a company that created HelpSpot, a web-based help desk software application. With over 19 years of experience in the industry, Ian has successfully navigated the world of software entrepreneurship. His journey is marked by his ability to find the right balance in product development, maintain user engagement through his blog, and his passion for good design. Here are a few of the topics we’ll discuss on this episode of Cache Flow:

  • The cost of advertising for help desk software keywords on Google can reach up to $140 per click.
  • Exploring alternative advertising platforms, like Microsoft Ads, can offer more cost-effective options.
  • Balancing the cost of customization with the potential benefits and impact on overall product development is crucial.
  • Leveraging existing customers as brand advocates can drive word-of-mouth referrals and attract new customers.
  • Productizing services and entering the SaaS world is a common goal for companies, driven by the perception of higher profitability and recurring revenue.
  • The number of answers a person can provide in a day varies, but it can be as high as 80 or even hundreds.
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Connect with our host, Brian Dainis:
  • 09:02 – “And so kind of our core bread and butter customer would be like a big company where we are in a department of IT or a medium-sized company where we are the entire customer-like support platform. But it also has a lot of, so that’s like your traditional like standard IT use case, like an IT organization uses IT to manage it ticketing for people with IT problems. Then there’s also the other side of it, which is sort of just end-user customer service. So you sell a product and you’re just managing those primarily email accounts in our case where people are maybe asking for refunds or questions or whatever the case may be. And HelpSpot manages all that for you.”
  • 15:27  – “And then when you get a click or whatever. It’s like not usually a person who’s just going to buy right there. It’s often they’re researching and then they’re going to go bring it back to the committee. The committee’s analyzing several options. They have a list of questions, so we do get people who just show up and buy, but that is definitely the exception to the rule. It’s usually more of they want a demo and that whole kind of thing. So it’s a little bit different than what a lot of people might have, their SaaS these days where they’re really optimizing for total self-service and people being able to convert instantly. Because the decision maker is the one on the page. That’s very often not the case for us that the decision maker is the one looking at it.”
  • 21:34 – “There can be stuff along those lines with customer-specific stuff I’ve always done, we’ve given them the option to basically… we’ve only actually done this maybe four or five times, but if they really needed something and they’re like “we’ll pay you for it”, whatever. And we have professional services too, which will just do stuff with our API and things like that. And I have given people in the past the option to basically move something to the front of the line. So it’s like still our IP, we own it, but we’ll add this feature for you, but it’s going to be $5,000 or $10,000 or whatever, just basically prioritize it and then we will add it as a feature rather than building it like as something through the API or whatever.”
  • 27:23 – “We’ve always had a strong kind of word of mouth. The help desk is the kind of tool, unlike a lot of SaaS tools, really even B2B ones, where people are using it 40 hours a week. They come into work and they use HelpSpot. And then they use HelpSpot all day long until they leave work. And so there is like a stickiness there where they’re going to take it with them to other jobs. So that’s also always been the other big avenue. It’s just managers or people who become managers in other jobs and they’re like, “Hey, I used HelpSpot at my last job and it’s great”. And they’re coming into an organization that either isn’t using anything or they’re using any something that’s not supported anymore or whatever and or built in-house.”
  • 32:25 – Brian: “We still close deals all the time from cold email and LinkedIn and yeah, it comes in all the time.”
    Ian: “Give me your top two or three tips here.”
    Brian: “So you have to be very specific. So your campaign has to be like, so niche and so tailored and then the messaging has to be so niche and so tailored that the person reading it questions if possibly like, you actually handwrote the email. Don’t do links or any images in the email”
    Ian: “Just a plain white email.”
    Brian: “Yeah. Plain white email. Make it look like you sent it and then I’ll put like font for the logo and just like color the font, the color of the brand. So it kind of looks like a logo, but it’s just like a font logo. And then just keep it like really strips down basic email short like three to five sentences. Do like five to seven touch points over a month or two.”

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Episode Sponsor

This episode is sponsored by Curotec, a software development solutions provider, offering both project-based application development and staff augmentation services. Global top consulting experts in Laravel, Vue.js, and enterprise WordPress development services. Contact Curotec today to discuss your next development project, or to augment your in-house team with top talent. 

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