Hey Nick,
It’s great to know you’ve built a strong company with remote teams.
How do you get to bring cross functional teams align towards the common goal ?
As founders, you set a direction for the quarter/year and how is that being communicated in unison and everyone in the company are in the same page especially when they get busier in their daily individuals tasks?
Great questions, Rajaraman! First off, I really love being in a crowded market. It means there’s a big opportunity, the market/problem set are validated, and you have to be creative to stand out.
Having fewer people and fewer resources than other companies in a large market has been a beautiful constraint in my experience. It forced us to focus on a specific segment, be thoughtful about how we used capital, and to make big bets on the brand.
From a distribution standpoint, I describe it as doubling down on things you can’t write a check for. We can assume all our competitors are very smart and will out-spend us when possible. But there are many marketing channels you can invest in that require commitment and effort – you can’t just write a check to be successful. Content marketing is my favorite, and we have invested most of our marketing efforts up to this point in content. Our friends at Wistia have a term called “Brand Affinity Marketing” and we’re big fans of using these sorts of tactics to stand out. Along those lines, we’re currently working on a short documentary series that I’m very excited about.
In terms of differentiation, we tend to over-estimate the power of feature functionality in the buying process. Your company should probably be talking more about why your values mirror your customers’ values. Often times people like to buy from companies that share their values and have a similar view of the world.
For instance, there are many ways to view customer service as a business – we differentiate by saying that we built Help Scout for the world’s most customer-centric businesses. We believe customer service is your most effective marketing tool, and we’ve created products that embody those values. Companies that aren’t onboard with that should probably choose something else. It’s an asset for your brand to have an opinion, and to seek our specific types of customers.
The point is to make it about who you are more than what your product does. I can buy a jacket from hundreds of companies, but I always buy from Patagonia because it’s a company with values that speak to me on an emotional level. That’s the foundation of customer loyalty.
Hey Jared, from day one we wanted to bet the company on our content strategy. Content is a way for us to do brand marketing, build organic SEO volume, and build an audience with our newsletter. Outside of focus on content, we were entirely focused on the market, our ideal customer profile, and iterating on the product.
Word of mouth is everything, and there’s not really anything better for word of mouth referrals than a good product and good content.
Hey Joshua! Awesome regarding the B Corp stuff – love it.
Honestly I feel like we still have a lot of positioning and messaging work to do. It’s a really difficult thing to do well. If I could do anything over, I’d build a product marketing function way earlier. I didn’t fully appreciate all the value those folks add to the business until recently.
If I were in your shoes and didn’t have the resources to invest in building a product marketing function, I’d start getting on sales calls and reaching out to existing customers that match our ideal customer profile, and I’d start asking them to describe the product, describe their favorite thing about it, tell me what problem got solved when they implemented it, how it made them feel.
The most effective version of our home page was actually one that didn’t have any messaging in the header – it was just a direct quote from a customer. The goal of good messaging is to frame the problem and solution in words your customers would use, so when all else fails, use your customers’ words. 
We’ve spent a lot of time thinking about whole company support! One thing that’s easy to do right away is to have new employees spend significant time in the support queue during their first couple of weeks. For us it’s really important because it’s a way to become familiar with our product AND our customers.
Kristi from our team recently published an amazing post about how we do whole company support in a 100+ person company. We’ve iterated on the program a bunch and it works super well today. I recommend giving it a read!
Hey buddy! I’m excited to catch up next week. 
Thanks for the question.
The B Corp certification process was rewarding and I’m glad we decided to do it. There are two big steps: legal changes and the certification process.
The legal change is converting from a Delaware C-corp to a Delaware Public Benefit Corporation (PBC). Many states support some form of PBC these days. I won’t get into the specifics, as they may vary by state, but what I love about the PBC in principle is that you have three fiduciaries: customers, beneficiaries of your public benefit (in our case the small business community), and shareholders. In a C-corp you only have one fiduciary: shareholders. We’ve always made decisions with all three fiduciaries in mind, so it felt like the PBC was a better fit for our company.
The certification process is much easier than a HIPAA or SOC-2 audit, but similar in that much of it is about documenting process and procedure. I like that it forced us to get creative and create a few new programs in the company that enable us to give back. For instance:
The only thing I didn’t love about certification was that it seemed a little unfair to a company that’s fully remote and doesn’t manufacture any physical goods. I’d love to see some improvements made in that area, but ultimately we were still able to get a high enough score to be certified.
All of the above are challenging in that they are time-consuming. But as a company we felt it was a worthwhile investment and I have no regrets.
Hello Vengat! You’ve made a keen observation:
on your landing page, this differentiation does not seem to be a big focus.
We have work to do. Our product has changed a lot over the last two years. We’ve launched live chat, in-app messaging, and are now in the process of launching several new CRM features. It’s fair to say that our go-to-market positioning hasn’t really caught up to how our product has evolved.
We’ve built a 2-person Product Marketing team in the last five months to address these challenges and better differentiate our go-to-market message. As you observed, we have a clear message internally about what makes us different, but we should do a better job communicating it on our website.
One of the smartest people talking about this topic is a woman named April Dunford. She wrote a wonderful book called Obviously Awesome, which has more great advice about positioning that I’d ever be capable of articulating. I’d highly recommend checking it out!
Hello Rishab, thanks for the question. There are 3 reasons I believe per seat is the best business model for this type of product:
It doesn’t meter engagement with the product. If at all possible, you don’t want pricing to discourage engagement.
It’s predictable and within your control. Metering by customers fails #1, is very difficult to estimate/predict, and guarantees that your bill keeps going up in a way you don’t really control.
We are not the market leader, and the market is already accustomed to comparing products based on the price per seat. It causes unnecessary complexity in the buying process if the customer isn’t easily able to compare on price.
Is per user perfect? Absolutely not. But it’s simple, it’s predictable, and it enables us to maintain good margins.
Hi Nick,
Thank you very much for your excellent answers and insights. I could not agree more with what you have said.
The first two issues I brought up are typical for the transportation industry and in a way a special case. It is often easier to work with other functions. For example, operators often spend ten hours during an eight-hour day because of the issues that we address. They have little appetite to add an eleventh hour to their day in mere hopes of getting out of the treadmill or in anticipation of just getting more work if they become more efficient. In regard to finding the right customers and offering the right value, we have found at times that we were also just not talking to the right person.
Again, I truly appreciate your time and thoughts. Thank you very much!
Cheers, Chris (www.truckl.io)
Hello Sowmya, thanks for the question! I’ll refer you to this previous comment for more information about creating our core values.
Staying focused on values as you grow is difficult, whether the company is remote or co-located. At a high level, what I’d tell you is to commit to not allowing them to be compromised. Values are worth being stubborn about.
This means you hire for values, fire people that don’t embody them, and make strategic business decisions with them at the forefront. It’s an everyday commitment. It’s also very possible to strengthen them as you grow. I feel that’s definitely happened in the last three years at Help Scout.
Hello Varun, congrats on your incredible growth! Growing at that rate can most definitely be a shock to the system, even if you do it really well. 2 
40 in 12 months is a lot.
What I tell people is that in a remote team, at 25 people you’ll need the organization, process, and procedure of a 100+ co-located team. While that may sound like a negative thing, it’s much easier to create and implement this stuff when the team is smaller. I’m guessing cross-team collaboration is a big challenge you are facing, which typically points to a lack of clarity around process and procedure.
Many companies underestimate the investment required in their people. You can’t just hire people to built the product and expect them to work well together – you have to hire folks that focus solely on the team and culture as well. In my experience, building a culture is no easier than building a product.
At 40 people, I’d have 2-3 people on the team fully focused on what we call People Ops. It includes HR, hiring, and talent management. Hire really good people whose success measures include supporting the team and solving some of the challenges you identify.
In a separate comment I mentioned the success we’ve had bringing in program management as a function:
One thing that’s been a game-changer is hiring a technical program manager to help the team work better across teams and complex projects. If I were to do it over, I’d bring this function in way earlier.
I’d also give that some thought. People Ops and Program Management will enable your team to solve hard remote challenges. You’ve just got to think way ahead in terms of making those investments.
As for hiring, I always caution that going remote is not a cost savings if you do it right – the costs are merely distributed differently than a co-located team. It hasn’t been my experience that hiring is more difficult or expensive. We get far more applicants than co-located teams and typically better quality because of the much larger hiring pool.
At your size, I think it’s worth having one in-house recruiter. Posting on job boards doesn’t typically get you very far. Otherwise I’d have to get more specifics to offer any further advice.
Hey Ravi, these are good questions. I’ll do my best to answer briefly.
Ultimately what I’ve tried to do is build a company people are proud to be part of, and a culture within which they feel like they are doing their best work. Retention is the byproduct if you get those things right.
What I like to tell people is that it’s way easier to create liquidity for employees and shareholders than it is to build a great business. Focus on building a great business and you’ll find abundant ways to manage the liquidity situation.
Hey Dare,
The trick isn’t tooling – it’s outstanding managers. Outstanding managers know how to measure productivity holistically, and software doesn’t. In my experience, people management is way harder on a remote team. Being an individual contributor is easy, but management is very difficult. We’ve found that a full-time manager can partner with 6-8 people, but not more than that. My wild guess is that you have too many individual contributors and not enough people focused on your people.
No. Equity is one of many many variables. To pull from another comment:
What I’ve tried to do is build a company people are proud to be part of, and a culture within which they feel like they are doing their best work. Retention is the byproduct if you get those things right.
Hello Praveen, thanks for the question. We use a framework called OGSM. My good friend Dave Balter introduced it to me many years ago, and here’s a slide deck he did about it.
It’s not about the framework as much as it is your effort to communicate really well. We do an all-hands “Town Hall” meeting every month or so, and every quarter Shawna (our CFO) and I do a review of the OGSM and outline any changes. Every one of these meetings is recorded and available for folks to watch if they were unable to attend.
Because we all love building software, sometimes we make the false assumption that software can align teams. In my experience, good people and good managers can align teams – software is merely a delivery vehicle.
Hi @nickfrancis, thank you for joining us for the AMA and answering the questions in such depth! I’m sure these insights are going to be very helpful. 
And thanks to everyone who participated in the AMA. Hope to see you around for the upcoming AMAs as well. Stay tuned!
@Sofia, @Chris, @jaredf920, @selflessly, @brendan, @Vengat, @rishab, @sowmya, @varun, @raviramani, @Dray, @praveen. 
Thank you so much for such a thoughtful and detailed answer, Nick. As I read all the answers I can imagine this thread being a treasure trove to read anytime. Thank you for taking the time.
“doubling down on things you can’t write a check for” What a beautiful way to put it.
Dear Nick,
Thanks so much for your detailed response. I love your answers and all the helpful links. Wish you and HelpScout the very best in your journey.
Best regards
Ravi
Thanks, Nick! Appreciate the thoughtful answer. Shareholder value being the sole measure of a company’s success feels very antiquated. I love what you’ve done, and I love the goal of trying to get to 1% of ARR being given away.