The A to Z of Early-Stage Sales

Armando Mann, angel investor and former Sales VP at Salesforce, Dropbox, and Google hosted a talk discussing the nitty gritty of building out your sales strategy and team on April 1st, as part of the Pear’s speaker series. This is a recap!

Watch the full talk at, and RSVP for the next one on product management: August 18th with Nikhyl Singhal, VP of Product at Facebook.

You’ve built a product that has the potential to disrupt an entire industry, and now you need to get into the hands of customers. How can you do that strategically, and how do you build a team that can execute your strategy? Armando walks us through it all, step by step, with all the nitty gritty details you need.

Choosing Your Market
Maximizing Your Wins
Building the Machine
Set Up for Success
Key Takeaways

Choosing Your Market

Many founders think that the way to find product market fit is to distribute their product to as many people as possible and then see which groups are working out best. Armando advises against this.

“You never know who to hear or who to listen to when you’re getting feedback,” he explains.

Instead, you want to approach finding product market fit with a hypothesis of what problem you’re solving and for whom, and try to talk to the smallest, most narrow group of people that fit the bill. This might seem counterintuitive if you’re trying to build a big, category defining business, but starting small actually allows you to grow fast, if you choose carefully.

At Armando’s startup, RelateIQ, the team went looking for a market that they could win 9 out of 10 times, and that could grow and bring the company upwards. They considered their product carefully and kept narrowing and narrowing their target:

  • First, the team considered which workflows their product could support. Sales workflows were the best fit.
  • Tracking was the only feature their product had at the time (no advanced forecasting or revenue reporting). They knew this feature was valuable only to recruiting or partnership teams.
  • They didn’t want RelateIQ to be a recruiting tool. This narrowed the field to partnership focused teams.
  • The product only worked with Gmail. So, they could only serve partnership teams who worked in Gsuite. These were likely to be tech companies.
  • The product’s novelty, at the time, was the capability of extracting data from email, so customers would need to be comfortable giving access to their emails.
  • Finally, big companies would want various controls that the product could not provide. They would need to go after smaller businesses.

Taking all these factors into consideration, the RelateIQ team determined their target market: business development teams and tech startups with under 100 employees.

“That business could have been small and we would have died a small death in a niche market that was irrelevant, if that had been our only market,” Armando acknowledges.

But the RelateIQ team had a clear plan for how to grow quickly from that narrow market into the adjacent markets.

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“We knew what features we needed to go from partnerships to account management within a company. Then we also knew how to go up market from under 100 employees to under 1000 employees,” says Armando. “So, as we moved along the axes, we would unlock little pieces of the market to give us this beautiful up and to the right chart where every group was growing.”

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Focusing on narrow markets has the benefit of forcing focus and tighter referral loops. Once you’re growing in a niche, your cost of acquisition in that niche goes down, and you can afford to reinvest those savings into your next niche.

In sum: try to find your smallest possible market. It could be geographic. It could be the tech stack. It can be any dimension. Make your product incredible for that small group of people. Then, focus product marketing, sales, everybody, to go after that market.

“You have to be very clear, this is not a sales strategy, it’s a company strategy,” says Armando.

Once you have nailed that market — you’ve figured out the cost of sales, your sales cycle, all your key metrics, and they are in a healthy place, i.e. predictable and repeatable — you can seed the next one.

Note that whether you start down market and move up market or the opposite way doesn’t matter. The point is to figure out how to dominate a sub-piece of a market that can feed into adjacent markets.

“There’s not a bad market to go after first as long as these are customers that can stay with you,” Armando notes. “It depends on the strength of the entrepreneur, what you’re comfortable with and who you want to solve this problem for first.”

Maximizing Your Wins

Like many salespeople, when Armando first started in sales, he was introduced to the big myth of “Always Be Closing.” It was one of the biggest things that he had to unlearn.

“I thought you always wanted to get new customers, that was the thing. But that’s not right. In SaaS, renewals and customer success beat new business 10 to 1 every day,” says Armando.

That’s because great retention and upsells compound, so a small improvement in these metrics has a much bigger impact on ROI than a small improvement in acquisition. While the first few years of this strategy might not look too sunny, over time, if you hit your targets, you will fly past your competitors.

Armando recommends that you not worry too much about how you will raise prices over time for your first customers, and focus instead about how pricing will affect your next customers.

“Those first customers, you can always say, ‘Hey, this is the pricing. We’re new, we’re starting our business. Here’s what we aspire to charge,’ and then there’s a negotiation. You say, ‘We can do this for this year, and chat again at the end of next year at renewal time, or we can do a three year contract and lock in this price for the next three years. We’re not going to be a great company just by getting an extra 10, 20% from you every year. Wwe want to make sure that we have a long term relationship with you.’”

Make sure both your account executives and customer success managers take interest in the success of upsells.

Building the Machine

Hire a Customer Success Manager from Customer Number One

A strategy is nothing without execution, so it’s critical to think through how you will build and structure your sales team to accomplish the plan.

The first thing is to have Customer Success Managers. It may seem like a good idea for you as the founder to take on this role, but Armando advises against this, as founders usually need to be ahead of the curve and focusing on hiring, fundraising, and selling. Armando recommends you have a Customer Success Manager onboard from customer number one.

“That is the first group of customers that hits the one year renewal date. And that’s the data that VCs will look at after a year and say, ‘Show me your first customers. What happened in the last year?’ You could go and say, ‘We’re great now, cohorts are getting better and better. Those were just a bad fit, just don’t look at our data from our early customers,’” says Armando.

“It’s so much more powerful to say, ‘Look, these first customers, none of them have churned and they’ve grown to extra spending the last year and you can call any of them and see how things have gone over the last year.’ That’s a way better story. So from the beginning I would spend an enormous amount of time on my existing customers.”

A good ratio early on is one Customer Success Manager for every two Account Executives. When scaling, aim for one Customer Success Manager for every 1 or 2 million dollars of recurring revenue.

What to Look For In Your Account Executives and Customer Success Managers

For account executives in the early stage, you’ll want to be looking for athletes — “People that can build the plane as you’re taking off.” When you’re scaling, you’ll want to start looking for candidates with a track record of scaling with a company and can leverage all the structured resources that come with scale.

Let’s call the early stage account executives Jane, and the scale stage account executives Jack. Here’s what they might look like as candidates:

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The characteristics you are looking for in customer success managers as compared to account executives are actually very similar to the above. The difference comes in their respective motivations.

Armando’s uses a very simple test: say your employee gets an email from a customer at 11:00 PM at night before they go to bed, after watching something on Netflix. Both will respond to that email (though you might tell them not to and just wait until the next day!).

“The AE will do it because of the leaderboard, because of the competition. They want to close that deal.

The CSM will respond to that email because of empathy. They feel the pain of the customer. They’re like, ‘If I don’t respond to this person, they will have to wait 10 or 12 hours until I get to the office and go through my meetings and get to this email. If I respond to this email right now, I’m putting them out of their misery and just helping them out with this one problem. That one short email from me will help them unblock today.’”

Where to Find Your Early-Stage Account Executives and Customer Success Managers

Armando recommends a few sources to find the right early-stage hires, your Janes:

  • Unsatisfied large tech company sales professionals: “You’re looking at people that went to a large company because they thought they wanted to be in sales and they got the training and realized they didn’t like the structure and the constraints that came with being in a large company. They didn’t necessarily like the certainty that comes from knowing exactly what they had to deliver every few months.” Note that Jack candidates do love this.
  • Former entrepreneurs: “I don’t think there’s better sales training than being an entrepreneur, so bring those folks in who will appreciate that you have a product that you can sell and that there is traction. They were some of the most loyal sales folks I’ve hired because they understand how difficult it is, what you’re doing as an entrepreneur. They can empathize and they know what they need to deliver for you.”
  • Business development, private equity, or venture capital professionals: “They have a lot of acumen. They have to hustle to get into certain deals. They have to be creative. There’s no playbook.”

If you’re looking for Jacks, you’ll want to investigate sales candidates who have spent 3–10 years at large companies (either one, or several) developing their skills. You can also find them in lateral industries. For example, if you are a FinTech entrepreneur, you might try to look for sales professionals in commercial banking instead of in tech. These professionals will already be well-trained in the fundamental principles of successful sales, and all you’ll have to do is to teach them the technology side of it.

Don’t worry too much about industry expertise. Unless your product is in a regulated industry or a very hardcore technical product, your hire should be smart and able to learn quickly.

“I would rather bring somebody that has all the other characteristics that you want in your company — a teammate that will connect with your company really quickly and in a positive way and add to your culture.”

A great way to source for such high potential candidates is to ask for referrals from your engineers. Ask who they might have met at their prior companies in sales.

“Most would be like, ‘I never met one. Sales? I don’t know those people, they’re in different building.’ But if they met somebody, that in itself is rare enough that you would take that as a huge plus — that this salesperson was able to connect with engineers or with PMs or with other teammates.”

Moreover, if they’re hired, they also will now have a friend and built-in sponsor inside your company.

Set Up for Success


When you’ve got great candidates, you want to make sure that they are able to work as well as possible with your existing team. Armando goes as far to make sure that high potential candidates meet over 10 to 12 people early on in the interview process.

“It’s a massive overkill, unless you realize that what you’re building is a group of folks who are all collectively responsible for this hire. So when this person joins, they all feel a level of connection or responsibility for this person’s success, which is incredibly valuable.”

Once the candidate joins, do all you can to help them form connections as quickly as possible — scheduling breakfasts for them, assigning them lunch buddies, etc.

“At a high growth startup after months two and three, you cannot claim you’re a newbie and you want to connect with somebody because you haven’t met them before,” says Armando. “You need to build the network in the first few weeks when you don’t have a quota, you’re still learning, and meeting people is part of your job. Make that something structured in the onboarding process.”


Founder CEO’s tend to think of their sales process in a linear funnel, and thus often set up their sales teams in a straight line as well. You are probably familiar with the typical setup of having some SDRs (sales development reps) doing outbound and inbound sales and taking in calls, emails, or leads. Then the qualified leads get passed to the account executive who closes the leads. Then the sales engineers help with demos and setting up the test environments. Then the CSM handles post-sales.

While this kind of assembly line setup works for large companies that are more predictable, this will not work well for an early-stage company that hasn’t even found product-market fit yet.

Armando recommends organizing your initial hires instead into a pod consisting of a CSM, AE, SDR, and sales engineer, working together as a group flexibly and helping each other with workloads.

The first pod should then seed the next pods by each starting pods of their own, and hiring people into their new pods. This works because each of these leaders have had the same experience and understand how to run a successful pod.

Armando is also a fan of having Product Managers join sales teams and getting in front of customers as well.

“PM’s bring a lot of credibility on the roadmap. As a salesperson, many times you don’t have the credibility with the customer to talk about the roadmap because they assume that you might not have the whole picture. When a PM comes in and talks about the roadmap, then you know it’s what they’re working on,” says Armando.


What type of employee incentive plans are practical for your first true salesperson? Should their options be tied to their sales performance? If so, what type of cash bonuses make sense at early stages in the company’s life?

“In my mind, they should be working and being motivated the same way the first support person, the first service person is, and the engineer is. They are building the company, so they should be incentivized in equity. That doesn’t mean that that’s going to be the comp plan for the rest of time at all. They should have a salary that is comparable to the rest of the team.”

For an early-stage company, tying bonus plans to sales performance might be premature.

“You’re creating a sense of predictability that you don’t yet have. So don’t lie to yourself or them saying that you know what you’re doing — because you don’t. You don’t know what this could look like. You could hit product market fit and hit it out of the park or not. Either way, you want them to pay the rent.”

At Dropbox, the first sales hires were at first compensated with sales performance bonuses, but were then switched to equity and salary compensation plans. The shift in turn led to a significant breakthrough for the company — automation of one-touch only sales.

Dropbox had a Contact Form, and many times, a customer would email through the form ready to buy and inquiring only about pricing. They would only need one follow-up email with the requested pricing information to convert.

Under the sales performance plan, sales reps were incentivized to want to claim those easy sales and get credit for them. After the switch, their mindsets were different. The measure of success was now better aligned with how much revenue the company made as whole.

The reps pointed out that those form customers were not interesting to close and were just easy money — so why not simply put up a Pricing link and other key information under the form so that customers could self-serve and buy without going through a rep?

“We did that and self-serve went up, and the leads that the reps were getting were more complicated, more interesting, and they were learning about more interesting sales processes. We could work with those customers in a more intense way, because all the easy customers would self-serve. And I could not have figured that out by myself,” says Armando.

Key Takeaways

  1. Focus on one market, dominate the market, and then expand from there. Have a vision of how you are going to do that and explain that clearly to your product team, your marketing team, your sales team, and your investors.
  2. Retention and upsells win over sales every day. Invest in customer success — bring in a CSM early. Don’t be cheap. Bring in great people. Invest in your existing customers.
  3. When hiring account executives and customer success managers, be thoughtful about the stage you’re in and what you need for your company today. A great account executive or customer success manager might be a better fit for you in the growth stage, rather than in the early stage, or vice versa.
  4. Organization matters. How you organize your teams and set them up will make things very different. You can seed politics and resentment or you can create units that behave like a Navy Seal team and work together to take over different missions.

A Scientific Method for Content Driven SEO Marketing

Mada Seghete, Co-Founder & Head of Strategy & Market Development at Branch hosted a talk on ‘Marketing With $0’ in April. This is just an excerpt! Watch Mada’s full talk for advice on viral, referral, community marketing, and more at

Many founders, when thinking about “doing marketing,” will immediately jump to thinking about Facebook or Google ads. Yet, organic acquisition methods such as viral, referral, or SEO are often much more effective and, even better, cost you $0.

Mada Seghete, who leads strategy and marketing at Branch, has run hundreds and hundreds of marketing experiments. Branch’s data has shown that ads are in fact, the least effective channels when compared to the more organic channels.

“It’s harder to do these things, because you don’t get the instant gratification of buying the user that is now on your website or your app, but the effort does pay off, because these people are more likely to convert and they’re more likely to stay with you for longer,” says Mada.

Mada Seghete, Co-Founder & Head of Strategy & Market Development at Branch

One of Mada’s favorite organic channels? SEO. She firmly believes that a good content driven SEO strategy can work for any kind of business. But it’s crucial to be scientific, so you don’t waste time producing content that won’t drive results.

Luckily for us, Mada was generous with sharing the scientific method her team developed at Branch.

Gathering keywords
Deciding on keywords to rank for
Producing content
On SEO “Hacks”

(1) Gather data on all the potential keywords you could be targeting.

Your first step is to compile a list of potential keywords for your company.

A good place to start is with the queries that are already leading customers to your website. You can see where your search traffic is coming from and what keywords you are currently ranked for via Google Trends.

The second place to look is your competitors’ keywords. To research this, you can use tools such as Moz or SEMrush.

From there, you can then brainstorm some keywords on your own.

For all the keywords you add to the list, you’ll want to track the search volume, keyword difficulty, and average cost per click. You can find this information using tools like Google Keyword Planner, Moz or SEMrush as well.

[To see samples of Mada’s keyword research at Branch, watch the full talk at]

(2) Decide which keywords you would like to rank in search results for.

Once you’ve mapped out the universe of potential keywords for your company, you’ll need to determine which words you want to work on ranking for.

At Branch, the team narrowed down their list to the top 200 keywords with the highest search volume. They then checked Branch’s current ranking for those words.

Finally, they grouped these keywords into different themes and came up with their own formula to “score” and prioritize which themes of keywords they would pursue with content.

Branch’s formula looked like this: {{Relevance score*40%}+{competitor urgency*25%}+{keyword difficulty*20%}+{avg rank*15%}}/{count of keywords}

Running through a structured decision process like this allowed the team to uncover and write about topics they might not have considered previously.

“We would’ve probably never written an article about ASA files — an app association file — but we wrote something about that because it came out in our keywords. We explained how Branch could help with that, and it drove a lot of traffic to us.”

In sum:

For a full explanation, watch Mada’s talk.

(3) Produce the content!

With a prioritized list of topics, it’s time to write.

Instead of spending money hiring a writing team, the Branch marketing team instead invited anyone in the company to write on any of the topics on the priority list. Those who wrote received a free t-shirt that said “Branch Writer.” Many team members from customer success and sales ended up writing great articles.

What About All Those SEO “Hacks”?

Now, you might be wondering about all those little algorithm hacks that you’ve heard about.

While Mada has discovered some tips and tricks from her experimentation (for example, how to strategically run paid ads to boost your SEO faster — details in the full talk), it’s important to realize that a good SEO strategy is fundamentally a long-term strategy.

It will take about 2–3 months for your content to rank (Mada tested this personally by translating all Branch’s content into different languages and measuring how long it took to get organic traffic on these pages). But if you do it right, the results are evergreen.

Hacks may work in the short term, but they won’t get you the long-term results you actually want.

Mada recalls a story:

“I remember Google changed their ranking, and I was sitting in a marketing leader group, and everyone was like, ‘Oh my god, I just had a drop of 20% of our organic traffic. What happened?’ And I was like, shit, what happened?”

Mada was in for her own surprise.

“Then I looked at our traffic, and our traffic had gone up, because the way we’ve done SEO is not by gimmicks and trying little things. We just rolled with content and if you write with content, Google won’t penalize you for that.”

Outbound Sales is *Not* Blasting Emails

Pouyan Salehi, Co-Founder & CEO at Scratchpad hosted a talk discussing effective outbound sales on May 26 as part of the Pear’s speaker series This is a recap! Watch the full talk at

What’s the best source for leads? How can I automate emails? What tools should I use?

If you’re putting together an outbound sales strategy and asking these questions off the bat, you’ve started off with the wrong questions, and you’re probably in the mindset of blasting emails.

Here’s what Pouyan Salehi, Co-founder and CEO at Scratchpad, has to say about that:

If you want to feel good about the number of people you’ve reached out to and say, ‘Hey, we’ve done activity top of funnel,’ then spray and pray is a great method.’ If you want good results, it’s not.

Why you shouldn’t just “spray and pray”

Why you shouldn’t just “spray and pray”

(1) Spray and pray creates operational debt.

In the early days of being a “zero” founder, the most crucial thing is learning what works and what doesn’t work. Once you know if something works, you can step on the gas and keep throwing more resources on it, you can do a lot more and automate more.

If you’re spraying and paying off the bat, you may get some responses, but because you haven’t put in the work to personalize and make the messaging relevant, you haven’t actually learned anything from the response. You still face the learning challenge, and you still need to do all the segmentation work.

(2) The results are usually just worse.

Just look at your own inbox. We’re all getting flooded with emails now, as more and more companies use automated systems.

(3) You can actually run into technical issues blasting emails.

So, let’s rewind and start with the three key components of great sales: strategy, data, and execution, in the correct order of operations.


The most important tool: your story. Start here. Often, this comes too late or as afterthought, but slowing down and spending some time getting your story right will pay dividends down the road.

Think of this story not just as an “outbound story,” but as your foundational company story, which can help you with fundraising and recruiting later. It captures the benefits and core problems you are solving and for who, what it is you’re actually selling, and how you are different.

The key components of a story are your headline and your messaging framework (pain, priorities, and motivations).

Your Headline

This may seem counterintuitive, but your headline is not what you sell. In fact, what you sell should come in last.

Your headline should instead be the benefit of what you sell, or the customer issues you solve. This is a subtle distinction from describing what your product can do or the features it has.

For example: Scratchpad is the fastest experience for account executives to update Salesforce, take notes and manage your tasks.

This is different from something like: Scratchpad is a Chrome extension that you can access and it’s a freemium model. This comes later.

Your Messaging Framework: Pain, Priorities, Motivation (PPM)

Now is the time to think about the people you are serving and break them out into personas. For each persona, you must deeply understand that they care about.

“Usually you can think about that through: what pains are they facing? What are their priorities or what are they motivated by?” says Pouyan.

Example: if your end user is a salesperson or account executive, it could be their top priority is hitting their quota. They’re also motivated by that because if they hit their quota, their job may be on the line. Another pain they have may be logging activity. They don’t need to do it to hit their quota, but their manager needs it so that they can understand what’s going on, which is annoying.

Don’t overthink this too much. When you’re starting out, just take your best stab and write something down.

Your messaging comes from your work here.

Note: this is not the time to be asking for email templates. Write your own! It depends on who you’re contacting and what it is they care about, or there could be multiple things they care about — which you should have discovered in your thinking above.

What to do if you’re a “zero” founder and don’t know what the story is yet:

This is common in the zero stage and it’s okay — still take 30 minutes to write down your best assumptions. You can come back and modify them as you learn.

This step is absolutely critical, as Pouyan points out:

If we can’t even get them to care about the problem through words, I wonder: why would we spend all this time building the product?

At Scratchpad, Pouyan created a one pager for this, just a “nugget” of a story that he eventually built around.

“In the early days we did a lot of outbound, but we did it solely to see ‘Can we get people to even care about this problem? Does this problem resonate?’ If it does, then it’s our job to solve that problem through a product,” says Pouyan.

This can be done even before you have product!

“You’ll learn a lot about what type of users might be more interesting to solve for first, who has the problem. Or maybe there was a secondary problem you never even thought of. It gets conversations going.”

Things to keep in mind:

  • Nobody cares about how awesome your product is, or who your investors are, or that you went through this awesome accelerator, or made this killer hire, or released a new version.
  • Make your story about them — your prospects and core customers. They need to understand what they are getting out of this and why they should care.
  • The more time you spend empathizing with users, understanding their problems and crafting messaging and, ultimately, solutions for them, the better your results.


You may be asking: Okay, *now* what’s the best data source? Where can I scrape leads? Where can I buy leads?

This section is short because the reality is: there is no one single best data source. It depends on who you’re going after and what industry they’re in — so use multiple sources. Then, clean the data and validate your emails.


Now is the time to combine your strategy and data to execute personalized and relevant communication at scale.

Relevance and personalization are different.

Personalization: “Oh, wow, I saw you went to this school. And we both grew up in this state and now let me talk to you about my product.”

Relevance: “Hey, I noticed your app is really popular in this country, but you haven’t localized it for this country yet.”

Personalization might involve mentioning things like first name, company name, and title in your email. Relevance is mentioning company competitors.

Relevance, in Pouyan’s view, is much more important than personalization, because it shows you’ve done your research and knows what your prospect cares about.

Keep it simple: your goal is simply to start a conversation.

At this point, you may be tempted to pack everything into one outbound email. Do not do this. Remember: you are not trying to get to all the way to close in one email. That’s way too much.

You might not even be trying to schedule that conversation on the calendar yet. Start small and figure out what works.

“The ask could simply be, ‘Hey, does this sound interesting to you?’ And all you’re hoping to get is an email response of ‘Maybe’ — just that there’s some signal on the other side that you can then use to strengthen the conversation,” says Pouyan.

Don’t ignore the neutral responses.

It almost never happens that a cold email is going to elicit something like “Oh, this sounds amazing. Please send me a calendar invite and I’m going to invite my whole team so we can talk about purchasing.”

More often than not, you will receive replies like: “No, thanks. Not ready right now.” “We’re busy. Can you please get back to me next quarter?”

Anything but a hard complete no, Pouyan considers a neutral response. These responses are signals that your messaging just didn’t land in the right area. Maybe it was close, but it didn’t quite hit the pain point.

Here, you need to be ready with objection handling. You need to have a response ready for “Hey, not right now, or we’ve already invested in a different solution,” and similar objections. Pouyan created a series of templates for these.

Unfortunately, we can’t give you the magic words that will get the results you want. That comes from hard work, and at ground zero, this work should be founder-led.

“You learn so much in terms of crafting that narrative, sending it out there, seeing what resonates. And you take that learning, not just for sales, but also in how you position your company. And how you position the product. And what you work on. So the effort has got to be there,” says Pouyan.

It’s like going to the gym. You just gotta show up, and then you’ve got a system for how you work out. You get into that flow.

Pear is Partnering with Gatsby!

Community is one of our top values at Pear. We believe deeply in the power of deep, authentic connections — it’s how founding partner, Pejman, went from being a rug salesman to a tech investor, after all.

Since the early days, we’ve devoted a lot of energy into nurturing a vibrant community of high-caliber founders, and we know how much work it takes. That’s why we’re excited to announce our new pre-seed partnership with a company seeking to empower the superheroes who do this important work: Gatsby.

Like all of the founders we back, Zach Rivkin is someone who deeply understands the problem he’s working on. As Joe Lonsdale’s Chief of Staff at 8VC, Zach had a hand in helping to manage Joe’s network. One of the most meaningful ways of nurturing relationships is to host intimate events, and Zach quickly became very familiar with the painful process of pulling such gatherings together.

“Let’s say there’s someone visiting from out of town, and you want to have a dinner with them, and maybe eight other people in your network. Who should you invite? How do you send those invites out? How do you figure out the seating chart? How do you track people’s dietary restrictions? How do you collaborate on this with other people in your team? There are lots of these small little things. I’d be back and forth all the time with the admins and executives trying to figure out how to work through these problems. And if these things break, it’s really bad!”

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As someone with a front row seat to innovation, Zach thought, why don’t we actually try to use technology to fix these annoying workflow issues?

Back in August, Zach had met his first cofounder, Michael Zuccarino: an engineer at Pinterest with a deep passion for building indispensable products. The two had already been building on the side for fun and loved working together. They then brought in creative technologist, Chris Zelazo, from Pinterest to complete the team as their third cofounder. Michael and Chris first worked together on a project for Apple to rapidly prototype a new feature in the Pinterest app, which was demoed and presented at WWDC ‘19.

The magic moment happened when these three builders aligned on the Gatsby vision: build a powerful technology system to serve the administrative workers who manage high-stakes, complex relationships and their related workflows, such as intimate event planning.

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You might be wondering why a good tech solution doesn’t exist yet, especially in such a tech-forward industry. We like it when our founders have some ideas:

“I think admins are somewhat trained to always make it look like everything is working seamlessly behind the curtain,” says Zach. “Also, I don’t think a lot of people ask admins for their opinions on what could be done better. It’s framed as a very execution oriented role as opposed to strategic, but I view a lot of this administrative work as highly strategic.”

We love that Zach has empathy for his users in spades.

“These admins are super powerful in a way that most people overlook. Their executives rely on them. They have tons of context and knowledge in their head, because they see everything going on. They own the keys to the castle and determine who gets meetings and who gets pushed forward.”

Indeed, we agree with Zach — it’s time to supercharge those powers with technology. We’re thrilled to be partnering with 8VC to back this incredible team.

How To Actually Be Helpful to Early-Stage Founders

This post is an excerpt from longtime startup mentor and Pear Operating Partner Touraj Parang’s onboarding session for Pear Accelerator S20 mentors — handpicked industry experts who we personally match with each founder in the cohort. Interested in being a mentor? Reach out!

Build the Foundation: Get to Know the Team On a Very Personal Level
Establish a Heartbeat
Be a Good Coach and Look to the Future

By now, “let me know how I can be helpful” is such a cliched offer to founders in Silicon Valley that it’s become a Twitter meme. Being helpful to founders is often framed as a means to “network” in the Valley, or to become a successful angel investor, but the best mentors, like Touraj Parang, do it out of true love for the founder journey.

Touraj began “mentoring” as an entrepreneur in the mid-2000s via getting together with other entrepreneurs and sharing best practices. After selling his startup, he began angel investing, and being helpful was a natural thing to do for the founders he invested in. Over time, he shifted to simply advising without investing for the love of it.

“I personally like to know: what are the latest technologies or what are people thinking about? How are they trying to solve these tough problems? I take satisfaction in being able to help other entrepreneurs achieve their dreams, paying it forward. Lots of people mentored me and helped me, and so I feel like that’s the way Silicon Valley works.”

Especially at ground zero, companies can barely look like companies. It’s a different ballgame from mentoring more advanced companies. Touraj draws on his hard-earned years of wisdom to share best practices for mentoring founders at the earliest stages of a startup.

Step 1 — Build the Foundation: Get to Know the Team On a Very Personal Level

Most early-stage founders are struggling to answer very similar questions or challenges:

How do we grow the team? Who do I need to hire? What do I look for in a new hire? Is it how much culture matters? How much of a stickler should I be about culture if I need someone now?

How do we find that product market fit? What is really even my core value proposition? Who is my customer? Do I sell to bigger customers and a more expensive product or to smaller customers with a cheaper product?

“A lot of these questions are very much existential. It’s just picking a direction and not knowing which way to head,” says Touraj.

Fundamentally then, mentoring an early-stage entrepreneur is almost like being a therapist. Your role is to help founders figure out what their values are and who they want to be in the context of their company.

There’s no right answer to these questions, and that’s why it’s so critical to know the team on a very personal level.

So, before you even get into the idea, the market, the competitive landscape and all the other fun things about the business you’re working with — really get to know your founders.

“You really want to try to see the world as much as you can from their point of view. Because then you can actually help put things in a language that they understand or motivate them in a way that they would really click with it.”

What is their background? What have been some past challenges or extraordinary achievements that they have had? What are their personal aspirations and ambitions? Try to probe into their areas of strength and what they consider to be their weaknesses, individually and as a team.

Understand what success looks like to your mentees. Capture their initial goals, even if they are vague, and start from there. Though many similar challenges come up with early stage founders, the founders themselves are likely all very different.

“I try to level set initially and understand, ‘Where are they coming from?’, and then be responsive to where they are, and meet them where they are, rather than just having uniform advice for everybody. I try to be very mindful and personalize the guidance I give.”

Step 2 — Establish a Heartbeat

Part of building a solid personal foundation with your mentees is to establish a rhythm of the relationship. Whether it’s a weekly or biweekly meeting, put it in the calendar right off the bat. Hold that slot in your calendar and make sure your mentees put it in their calendar and stick to it.

Once everyone gets busy, it can be very easy for the weeks to go by and lose that thread. While it’s understandable that the meeting may need to be moved occasionally, do all you can to hold your mentees accountable to showing up for the meeting, and make sure that you do your share and stay available as well.


Once you’ve established the basics, the key skill to being a successful mentor is to be patient and practice being an active listener.

Active listening to me is not only hearing what the person is saying, but then asking questions to get to the deeper layers of what they’re struggling with,” says Touraj. “It’s engaging in a dialogue and withholding advice until you understand the root cause and what the objective is that you’re trying to achieve in that conversation.”

When a founder first comes to you with a complaint about a situation, the root cause of that complaint is often not clear. Sometimes founders struggle because they’re not clear on what goal they need to achieve. Sometimes they know their goal, but they don’t know how to achieve it. Some founders are very detail oriented but have a hard time of going higher up and looking at the big picture. Some founders are so academic and big picture that they don’t really see the operational steps necessary to get where they want to go.

You want to create a space for open dialogue so that you can get a clearer picture on the situation.

Get into that mode of investigative work. Part of that is nudging them by asking probing questions.”

Some example questions Touraj suggests:

  • What do we learn from this outcome?
  • What hypotheses are we trying to validate?
  • Are there other solutions to the same problem?
  • What you’re putting your efforts into — is that the highest priority?
  • Do you have resources to be successful? If not, what do you need and in what order?

Note that through all of this, your role is NOT to tell your mentees what to do. Remind yourself to address the assumptions, rather than making assertions. Try to stay away from ‘You need to go do this.’

“It’s good for founders to know your role is not to provide answers, but to be a thought partner, to be a sounding board. Let them draw the conclusions. Once you clarify the assumptions and the goals, they can come up with how to get there and sometimes they come up with it much better than you could.”

If the founders are hitting roadblocks or feel stuck, a helpful approach is to suggest options. You might say, ‘In other companies I have seen, these are some of the things that others have tried. Which one sounds good to you?’

Touraj notes that newer entrepreneurs can be hesitant to open up about their problems.

“They feel like because Pear is an investor or potential investor in the next round, they always have to give the happy talk and seem confident,” says Touraj.

“You have to make them comfortable and say ‘Look, it’s okay. It’s okay if you have challenges. We have all had challenges, and it’s actually a good sign that you have challenges and you’re seeking help, rather than trying to white-knuckle it and then fail.’ They need to feel that they’re not being judged in any way, and that really, as a mentor, you’re here to help, you’re not a secret agent of the VC firm.”

Step 4 — Be a Good Coach and Look to the Future

When you’re working with early-stage founders, remember that you are also working with future leaders. As such, for maximum impact, go beyond the therapist role and take on a coaching mentality.

“It’s about seeing what skills we can give them, so that they become great entrepreneurs and leaders as their startup grows. I try to encourage a lot of reflection and self improvement,” says Touraj.

One way to do this is to train your mentees on best practices that you have found useful in your own life or in the organizations you have worked in. Although Touraj was an entrepreneur, many of the processes and frameworks he shares come from his experience at larger organizations like GoDaddy.

Touraj also works to hold his mentees accountable to their own goals.

“When we are meeting, I always make a point of writing down every goal, or every statement they make saying that they will go and do certain things. In my next meeting, I refer back to those and make sure to see whether they were done and if not, why not, so that they get this habit of accountability — if they say something, if they commit to something, they’ll follow through with it.”

In setting their own goals, however, founders may not be stretching themselves or taking enough risk. A good coach will figure out exactly how far they might need to push a founder. The best coaches help their protégés achieve things they didn’t know they were capable of.

“I think one of our jobs is to encourage founders to be bold, to experiment. And that it’s okay to fail and to learn as long as you learn from it.”