AI in Go-To-Market: Navigating New Frontiers

Our Zero to $1M conference wouldn’t have been complete without a session on how AI is changing the go-to-market (GTM) landscape. We recruited a panel that included seasoned entrepreneurs like Amanda Kahlow (6Sense and 1mind), Zach Vidibor (Octave) and Elaine Zelby (Tofu) and industry experts like Everett Berry (Clay) and our very own Kathleen Estreich (Pear VC). Our panelists universally agreed that AI-driven transformations in GTM will redefine team dynamics, optimize workflows, and unlock efficiencies previously unimaginable. Here, we distill some of the key takeaways from their conversation (scroll for the recording of their full convo!)!

Reshaping Roles and Workflows

Elaine Zelby of Tofu highlighted how AI can significantly reduce operational overhead, allowing companies to accomplish more with fewer people. Amanda Kahlow agreed emphatically as she introduced Mindy AI to discuss how AI tools are beginning to take on roles traditionally held by humans, thereby offering customers immediate access to information and engagement, and improving the software-buying experience.

Human + AI

While AI tools can perform arduous tasks much faster than humans, the panel stressed the importance of retaining the ‘human touch’ in GTM. Zach Vidibor from Octave expressed the critical importance of having empathetic folks in customer-facing roles who can deeply understand and address customer needs. In fact, the panel seemed to come to consensus that leveraging AI for data analysis while maintaining genuine human interactions could be the key differentiator for scaling startups.

Strategic Implementation of AI

For AI tools to be effective, they must be strategically integrated within a company’s GTM strategy. Everett Berry from Clay recommended supporting creative and strategic thinking with robust data management to ensure AI tools are effectively utilized to maximize ROI. Amanda Kahlow discussed the necessity of maintaining and updating data fed to AI tools to prevent reliance on outdated information.

In short, several actionable insights emerged for early-stage founders considering AI adoption within their GTM efforts:

1. Start with Clear Goals: Define a specific area within your operations where AI could make a significant impact. Consider starting with tasks that are time-consuming and mundane yet critical to GTM operations.

2. Leverage AI to Enhance Creativity: Marrying AI’s processing power with creative strategies can yield unparalleled efficiencies, making it immensely valuable to scaling startups.

3. Maintain Human Empathy: Ensure your human teams are empowered to do what they do best while AI handles the bulk of data-driven decision-making.

4. Iterate and Experiment: AI tools are evolving. Be prepared to experiment and iterate on strategy frequently to remain at the forefront of these technological advances.

AI is reshaping the sales and marketing landscape in real-time, offering startup founders potent tools to accelerate growth. By focusing on authentic, strategic, and thoughtful AI integration, early-stage companies can not only streamline their operations but also elevate their market positioning in this new digital frontier. As the panel beautifully encapsulated, the future of GTM lies in the harmonious blend of AI capabilities and human empathy. We’re excited to see what the future holds!

You can watch the entire conversation here:

From zero to 25M+ users: navigating the path to viral growth: lessons from Jon Noronha

Achieving rapid growth and successful product-market fit can be a maze filled with daunting challenges. For early-stage founders, embarking on this journey requires not only a solid idea but the perseverance to continually adapt and learn. The Gamma.app team has walked this arduous path from obscurity to 25 million users, and their inspirational story shared by Jon Noronha, Co-Founder and Chief Product Officer, at our Zero to $1M conference should be a beacon of hope to all founders currently in the trenches. 

Here are the key takeaways early stage founders can learn from Jon’s presentation:

Choose the Right Problem

Before diving into solution development, Gamma founders pondered a fundamental question: What problem were they truly passionate about and uniquely suited to solve? As they reflected, the process of creating and delivering presentations—a near-universal business challenge– stuck out to them. They considered it in light of all the pros AND cons and chose to pursue it because of the potential impact their product could have. For all early-stage founders, it’s crucial to love the problem you’re solving enough to be passionate about it for a decade plus of company building! And it’s critical to believe that you’re uniquely positioned to build that tool. Gamma founders were product leaders and they wanted to build a tool that would thrive via a PLG strategy to growth, to specifically play to their strengths. This is a great example of considering your fit to 1) build the tool and 2) build the GTM model to get that tool out in the market. Choose challenges that your team is inherently equipped to solve well. Build on those core competencies as you scale. 

Lead with Customer Motivation

One of the things that I loved most about Jon’s growth story was how he managed early customer onboarding, made it a point to spend time going through customer support tickets, and also was intentional about getting that customer feedback back to his team at Gamma. Jon shared:

“I was relentless about sharing [customer feedback with our team]… I made sure that every week our team heard five or 10 positive things that were going well. And we were getting some diehard fans out of this. We had a small number of true believers. And when I say a small number, I think like maybe 10 to 15 people who really got it and really believed and were telling their friends. Nothing to really write home about, but still it felt good to us!”

You can’t overestimate the importance of driving this motivation for your team, especially in the early days before you’ve really gotten to PMF!

Seize Luck and Keep it Real With Your Team

After some time of slow traction, the Gamma team ended up getting to a point of “existential dread.” The world was changing fast, with the economy going into a downturn and fundraising market drying up. Yet, amidst investor skepticism and financial pressures, the Gamma team had to take a big leap of faith in order to chart their course forward. They decided to integrate AI to enhance presentation design, tapping into a burgeoning trend, unveiling features that resonated and added unparalleled value to our users’ experiences. They would not have been positioned well to take advantage of the opportunity had they not invested so heavily in customer experience and awareness. What gave Jon and his team the confidence to take this big leap amidst so much uncertainty was the foundation he’d built with users and his team. He shared, 

“What’s interesting is this period of time of existential angst was probably the most productive and fun part of the whole experience of working on the company. I think there is a lesson there about being candid with your team about when it’s time to put it all on the line, I think it’s a card you can only play so many times and we had to play it, we had no choice. So we had a huge blitz of development.”

Jon and the rest of Gamma leadership had built enough trust with his team and customers to seize the opportunity AI presented, and this ended up being a pivotal step in them finding viral growth. 

Gamma Thrives

Entrepreneurship is a marathon, not a sprint. Gamma’s story highlights the importance of starting out strategically, remaining adaptable, and fostering a relentless spirit. By embracing setbacks as stepping stones and using them as learning moments, Gamma’s team navigated the complex early days of growth and product development. We are so grateful Jon joined us at Zero to $1M to share their inspiring story!

You can watch Jon’s entire presentation here:

In the next few weeks, we will be sharing summaries and recordings of the talks from Zero to $1M: Winning Early GTM and link them here:

Stay tuned for more!

Startup sales success requires unlocking the power of mindset: lessons from Jason Ferguson

In the challenging world of startups, the path to success can often seem shrouded in mystery and uncertainty, especially when it comes to mastering sales and growth. However, with the right mindset, even early-stage founders without a sales background can become the sales leaders their orgs need. In his inspiring session at our Zero to $1M conference, Jason Ferguson shared invaluable lessons on establishing a winning sales mindset, crucial for any founder aiming to go the distance. 

The Power of Pathological Optimism

Even when you’re doing well, a large part of navigating sales is dealing with rejection. Founders new to sales often get deterred and discouraged too quickly because the rejection can feel like a shock to the system! A critical part of learning to persevere is embracing “Pathological Optimism.” Jason shared how he first became a pathological optimist after a few early setbacks. Growing up with dreams of becoming an NFL player, he faced numerous challenges, from physical limitations to an inability to participate in fall recruitment. His unwavering belief in the possibility of good, even in the face of adversity, enabled him to seize an opportunity to meet the head coach of the University of Hawaii when things seemed most bleak. His ability to see and seize the opportunity allowed him to succeed against the horrible odds he was facing. For founders, adopting pathological optimism means seeing potential in every engagement and maintaining resilience in the face of constant rejection. Every founder must become a pathological optimist!

Embracing Radical Accountability

A cornerstone of having the right sales mindset is radical accountability—owning results and outcomes, regardless of external circumstances. For founders, this means looking inward for solutions and taking proactive steps to close gaps, rather than attributing failures to external factors. Adopting this approach fosters creativity and drives impactful action, positioning the company for sustainable growth no matter what challenges arise. 

Authenticity as a Sales Superpower

Jason underscored the incredible power of authenticity in sales. Having overcome athletic challenges and personal demons, Jason’s personal experiences shaped his approach to his professional challenges. It took him years, but eventually he realized he was at his best when he brought his full self to work and learned first-hand that authenticity pays off. 

Sales is often misunderstood, perceived as a field dominated by specific personality types. Yet, as Jason passionately conveyed, sales is for everyone willing to adopt the right mindset. The heart of successful selling lies not in adhering to stereotypes but in embracing an attitude of optimism, persistence, and authenticity. This is especially important for founders who might feel out of their depth in sales.

Real success begins when founders embrace their unique traits and principles, transforming them into distinctive selling strengths. By committing to authenticity, founders will forge genuine connections with their target buyers, employees, investors and more. Authenticity is a precious flywheel with endless benefits!  

A Call to Action for Founders

Establishing the right mindset is foundational to achieving sales and growth success as an early-stage founder. By cultivating optimism, embracing accountability, and leading with authenticity, founders can confidently navigate the complexities of selling and growth.

Remember, your mindset is the key FIRST step you need to take to win in sales and marketing. Engage with passion, act with intention, and lead with your true self. The journey from zero to success is yours to embrace.

You can watch Jason’s entire presentation here:

Thank you to Jason, for being such an inspiration to us and to founders everywhere!

Looking Ahead

In the next few weeks, we will be sharing summaries and recordings of the talks from Zero to $1M: Winning Early GTM and link them here:

Stay tuned for more!

In the meantime, if you are interested in learning more about Pear’s GTM Practice, check out our page here.

My journey with founder-led sales: lessons from Tracy Young

Sales—it’s a word that often sends shivers down the spine of many early-stage founders. With all the complexities involved in strategic sales, mastering sales can feel downright daunting. However, as Tracy Young’s journey with founder-led sales at PlanGrid demonstrates, effective sales techniques can be learned and applied, even if you’re starting with zero sales experience. During her keynote at Zero to $1M, Tracy gave founders in the audience a comprehensive guide to best practices and a dose of inspiration to help them see that they, too, can master the art of selling.

Her top insights are summarized below:

From $0 to $5 Million without a Sales Team: Nailing Founder Led Sales

Tracy Young didn’t start with a robust sales team or even a deep understanding of how to run one. Instead, her initial success at PlanGrid was driven by solving real problems for real people. Dealing directly with customers—from project engineers to superintendents—helped PlanGrid understand their market’s needs and show that their product genuinely addressed their core concerns.

Focus on Growth Levers

Tracy shared that it’s important to seek out “growth levers” by slicing your market in various ways to identify which areas are ripe for investment and growth. Using this approach, Tracy was able to discover what was driving growth for her customers and that helped her narrow her focus and pitch to attain rapid growth in the early days. In just one year, PlanGrid expanded from five to fifty hospitals, proving the efficacy of strategically leveraging growth opportunities.

Grassroots to Enterprise: Build from the Ground Up

As always, in sales you have to narrow in before you go broad. In the early days, PlanGrid aimed at solving individual project-level problems, which eventually opened the door to larger, enterprise-level deals. The lesson here? Scaling starts with small, targeted wins that build credibility and customer base. When PlanGrid finally landed enterprise deals, selling a thousand licenses at once became easier than selling five at a time. 

Focus on Customer Success from Day One

Achieving high net retention rates was paramount from even the earliest days at PlanGrid. For every dollar sold one year, PlanGrid could sell an additional $0.30 the next year—showing the importance of keeping existing customers satisfied and engaged. 

Show up with Determination and Expertise

Tracy emphasized three key traits for successful founder-led sales: determination, domain expertise, and the ability to sell. She shared a powerful message: at least one founder must embrace the role of sales. And not just partially. This founder must fully embrace sales with determination and a can-do mentality in order to go the distance. 

Creative, Low-Cost Marketing: Blueprint Suits and Donut Boxes

In the early days of scrappy marketing budgets, you can still stand out by employing creative tactics. For Tracy, that meant commissioning local fashion students to make blueprint suits in order to create a memorable presence at conferences. Another clever tactic involved delivering donut boxes with a card promising better food options for future meetings. These personal touches and human interactions stood out to her early adopters, and yielded significant ROI. 

Building Trust and Belief in Your Product

Tracy highlighted a crucial aspect of selling: belief in your product. She advised founders to build something people want and to believe in the power of their product. Authenticity resonates with potential customers—they can tell if you genuinely believe in what you are selling or if you’re trying to offload something subpar.

The Resource You Can’t Waste: Time

Time is the one resource founders can’t afford to waste. Tracy emphasized creating efficiencies, whether through product development or customer interactions. Listen more than you speak, answer directly, and always know the next steps before leaving a meeting.

Championing Your Customer’s Needs

What stood out perhaps most profoundly from Tracy’s talk was her sincere commitment to her customers—the ones who “took showers at night.” The best founders are champions for their customers, solving real problems, and providing tangible solutions and aligning their customers’ success, motivations and aspirations with their own. 

Conclusion: Believe in Your Journey

Learning to sell is a journey every founder must embark on. Tracy Young’s story is a testament to what can be achieved through determination, innovation, and an unwavering belief in your product. Take these insights, apply them to your venture, and remember: you can learn to sell, and you can achieve remarkable growth before hiring in GTM.

Stay tuned for more stories and insights from Zero to $1M: Winning Early GTM as we continue to share the strategies our amazing speakers shared to drive startup growth.

In the next few weeks, we will be sharing summaries and recordings of the talks from Zero to $1M: Winning Early GTM and link them here:

Stay tuned for more!

About Tracy Young:

Tracy Young is the co-founder and CEO of TigerEye.Tracy is an experienced company leader with a successful track record in scaling private enterprise technology companies. Previously, she co-founded and served as CEO of PlanGrid, the leader in construction productivity software that Autodesk acquired for $875 million in 2018. During this time, Tracy led the company through years of massive growth — from inception to product-market fit, and from $0 to $100 million in annual recurring revenue (ARR) — and drove teams to execute on strategic business initiatives.

In 2018 Tracy was recognized by Forbes’ Top 50 Women in Tech and named a Top 50 SaaS CEO by the SaaS Report. She has previously spoken at TEDWomen 2020, Techonomy, Salesforce’s Dreamforce and SaaStr.

Young was previously a visiting partner at Y Combinator (Winter 2020, 2021). She holds a B.S. in construction engineering management from California State University, Sacramento.

Zero to $1M: Winning early GTM!

Last Thursday September 5th, we hosted our first Zero to $1M: Winning Early GTM summit focused on supporting early-stage founders in their journey to master founder-led sales and founder-led growth. 

We opened the day with an invitation for the early-stage founders in attendance to think of the conference as their personal sales kickoff (SKO). SKOs are strategic meetings at established enterprise companies that usually take place at the beginning of the year to reveal the company goals, celebrate successes and recognize and reward top team members. These are very high energy gatherings, where everybody takes part.

As we planned the conference, we knew we wanted founders to treat the day as their personal SKOs. The early days of a startup can be so lonely and scary. Early-stage founders struggle to navigate the intimidating world of sales and we organized this conference for the very purpose of bringing founders together to learn, share best practices, and drum up the courage to crush founder-led sales and growth.

We had a full house throughout the day with amazing energy from both speakers and founders. 

Our morning sessions were filled with personal stories, learnings and mistakes from the founder-led sales/growth journeys of Tracy Young, Jo Phillips, Jon Noronha, and Sam Adeyemo. We also had a session on how to cultivate a winning sales mindset (especially relevant for technical founders who have never done sales) led by the amazing Jason Ferguson!

Before we broke for lunch, we had a special surprise: we gifted Rose Punkunus of Sudozi (Pear portfolio company) their very first gong!

Before unveiling our surprise, we explained the 4 stages that we walk our founders through in our hands-on GTM support at Pear (outlined below) and then announced that Sudozi would receive a Gong on stage as we celebrated Rose’s growth and “graduation” from the FLS stage and on to the expansion stage.

We are so proud of Sudozi’s progress and know they are just getting started. We were thrilled to see Rose hit the Gong for the first time on our Zero to $1M stage!

In the afternoon, we designed a “Choose your own adventure” program where founders could attend breakout sessions that were most relevant to their needs and stages. We had sessions around pipeline management, pricing strategies, selling to developers, customer success fundamentals, and AI and the future of the GTM tech stack.

We closed the day with a fireside chat with the two-time unicorn founder Sanjit Biswas, known for his work at Meraki (which was sold to Cisco for $1.2 billion in 2012) and Samsara (NYSE: IOT, $26B+ market cap). Sanjit walked us through his journey in transitioning from PhD research to becoming a successful entrepreneur in the tech world, focusing on how he learned sales and how he approached sales-led and product-led growth at Meraki and Samsara.

Thank you to all the speakers for being so generous with your time and for filling the day with rich insights and inspiration for the early-stage founders in attendance. Tracy Young Joseph Elias Phillips Jon Noronha Samuel Adeyemo Jason Ferguson Stevie Case Armando Mann Rosie Roca Rich Liu Josh Greene Nelson Bostrom Elaine Zelby Amanda Kahlow Everett Berry Jessica Ko Jessica Gilmartin 🔮 Sandy Mangat Zena Davé Zach Vidibor Kerry Wang Kyle Poyar Kathleen Estreich Keith Bender.  

In the next few weeks, we will be sharing summaries and recordings of the talks from Zero to $1M: Winning Early GTM and link them here:

Stay tuned for more!

All in all, it was a 10/10 day! We’re overjoyed by the amazing feedback we’ve received from founders in attendance. A couple examples include:

We are inspired to continue to support founders in their early GTM efforts, and already can’t wait for next year’s Zero to $1M conference!

Last but definitely not least, we want to thank our sponsors Cooley LLP, Banc of California, Amazon Web Services (AWS) and Remote for supporting this initiative.

If you are interested in learning more about Pear’s GTM Practice, check out our page here.

Debunking common myths: what technical founders need to know about sales

As a technical founder, you’re no stranger to challenging assumptions and pushing boundaries. Yet, when it comes to sales, many technical founders fall prey to common myths and misconceptions about sales that can hinder their startup’s growth. Let’s debunk these myths and uncover the truth about sales:

1. Myth: A Good Product Will Sell Itself, so I don’t need to worry about sales: Especially from a technical point of view, it’s easy to believe that if you’ve built a great product, customers will come flocking. While a strong product is undoubtedly essential, it’s not enough to guarantee success. In reality, ideas are cheap, and execution is critical. Competitors will inevitably emerge, and without a solid sales strategy, your product will get lost in the noise– even if it’s better than the alternatives. Early sales are crucial for validating your idea, learning how to talk about it and gaining traction in the market. 

2. Myth: I Can’t Sell Because I’m Not “Salesy”: Many technical founders shy away from sales, believing it’s a skill reserved for natural-born salespeople. However, this couldn’t be further from the truth. In Geoffrey Moore’s “Crossing the Chasm,” he highlights the importance of early sales to tech enthusiasts – a group that technical founders are uniquely positioned to identify with and sell to. Your deep understanding of the product and its technical intricacies can be a powerful asset in connecting with early adopters. Sales isn’t about being pushy or overly charismatic; it’s about building relationships and solving problems. 

3. Myth: Sales Is a Necessary Evil: Some technical founders view sales as a necessary evil – something to be delegated while they focus on building a product-centered company. However, the best businesses understand that success lies in being customer-centric from the get-go. Sales and technical teams should work hand in hand throughout the lifetime of the company, both driven by a shared commitment to delivering value to customers. Interweaving the shared success of both teams early on fosters collaboration and ensures that the customer remains at the heart of every decision. Ultimately, the most successful companies recognize and appreciate the unique contributions that both technical and sales teams bring to the table.

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Technical founders must challenge traditional myths about the sales profession and recognize the pivotal role that sales will play in their startup’s success. A great product is just the beginning – it’s how you sell it that sets you apart. Embrace sales as a strategic imperative, leverage your technical expertise to connect with early adopters, and build a customer-centric organization from day one. By doing so, you’ll pave the way for sustainable growth and lasting success.

Want to know more about leading GTM as a technical founder? Check out our additional resources for technical founders here

Building an effective sales strategy: Part 3 – Crafting the perfect customer pitch

Pear’s Partner, Pepe Agell, learned the importance of mastering sales during his entrepreneurial journey with Chartboost, a mobile advertising company. Pepe led Chartboost and built sales and go-to-market strategy for the company from its earliest days to its acquisition by Zynga in 2021. He is now a Partner at Pear VC, based in Barcelona and focused on Pear Europe.

This is the third part of our three-part series on building an effective sales strategy, focused on three essential stages of the sales process founders need to master. Before diving into part two, don’t miss part one and part two!

Now that you’ve learned how to run your client meetings effectively, let’s talk about how to construct the perfect sales pitch.

One of the most common mistakes I see is that sales people will often launch into the finer details of the product offering without sharing the bigger vision first and the impact that the solution can have in the customer’s life. Here is how I recommend structuring your pitch to most effectively close deals:

1. When pitching to a client, start with the why before focusing on the how or what.

After you gather as much information as possible from your client, you are ready to pitch your product. I like to follow the why, how, what method.

Simon Sinek has a well-known TED talk all about how great leaders talk about their products by leading with the why. I go back to this TED talk all the time, and I’ve found that the same framework can be applied in sales when talking to clients about your product or solution.

Why: You should lead with a strong explanation of why your solution is the best for the customer. This can include who you are, what is happening in the market, the challenges you’re solving for, and why the customer should listen to you.

Example of a strong why statement:After watching my dad go through diabetes and battle with insurance companies to get the treatment he needed, I was compelled to start a company that made it easier for elderly adults to navigate the health care system. I found that I had to be my dad’s advocate, calling and negotiating on his behalf, and I realized that not every older adult had that same support system.”

How: Next you can explain how you’re solving the problem the customer has, what your approach is, and some of the details about the product.

Example of a strong how statement: “We decided to build a marketplace where patients could easily onboard their medical information and get paired with the most suitable insurance provider in just few minutes.”

What: Finally you can dive into the what, really explaining what benefit your customers will receive with your help (revenue growth, etc.) and the specific features you offer.

Example of a strong what statement: “For every patient request we get on the platform, we process thousands of insurance quotes and select the most appropriate one for each case. We manage the contractual process, payments and medical claims. All in one mobile app.”

2. Get to a demo as quickly as possible.

Product demos help clients picture your solution in their daily workflows. It is also a clear way of visualizing how are you really solving their problems. From my experience, aha moments and even wow moments in a sales pitch happen during the course of the demo, not while going through slides. That’s why, I strongly recommend to get to the demo part as quickly as possible.

3. While explaining your product to the client, integrate your client into the story.

Slides need to connect to each other through an overarching narrative or story. It’s also important to bring your client along on the journey.

I’ve seen many salespeople feature the client’s logo on the opening slide. That’s great, but it’s much more impactful if you bring the client into your entire story. You can feature pictures of their products, their people, and statements they’ve made. Don’t forget to clearly explain what’s it in for that particular customer or for similar companies that are already working with you (see next point). Remember that your clients don’t care about your product features but the impact that you will have in their day to day.

4. Show proof of benefits from other clients.

I’ve found that it helps to share how other clients have found success with your product, but I recommend talking from a client’s perspective.

Instead of saying: “Our product is really strong at automation, and that’s why clients go with us.”

Try something like: “Clients in a similar growth phase experienced exactly the same pain points, but by implementing our automation tools, they were able to become 50% more efficient.”

5. Explain the next steps and how to get there.

Make sure you clearly explain the onboarding process, using screen shots where necessary, so the clients can really grasp what onboarding your product actually looks like. You should clearly explain how long it will take for the client to go live with your product. Also, if you haven’t already discussed pricing, make sure you do that before you wrap up.

6. Engage your audience meaningfully.

During the sales pitch you shouldn’t just ask “Any questions?” Instead, you’ll get more engagement if you ask meaningful questions like “Does this resonate with you?” or “Do you experience something similar?”

To sum it up, all founders have to implement a successful sales strategy in order to truly succeed. These are the best strategies I’ve developed while building and leading sales teams across regions. I hope they help you be more effective in getting new customers and growing revenue. And remember that “when the pressure is on, you don’t rise to the occasion. You fall to the highest level of preparation.”

This is part three in our series on sales!

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Building an effective sales strategy: Part 2 – Preparing for a customer meeting and leading it effectively

Pear’s Partner, Pepe Agell, learned the importance of mastering sales during his entrepreneurial journey with Chartboost, a mobile advertising company. Pepe led Chartboost and built sales and go-to-market strategy for the company from its earliest days to its acquisition by Zynga in 2021. He is now a Partner at Pear VC, based in Barcelona and focused on Pear Europe.

This is the second part of our three-part series on building an effective sales strategy, focused on three essential stages of the sales process that founders need to master. Before diving into part two, don’t miss part one!

Once your outbound sales efforts have been successful, it’s time to prepare for the meeting and lead it effectively. That starts with thinking carefully about how to use the short amount of time that you have with a client. My suggestion is to allocate your time according to the Pear Guide for Sales Meetings.

The Pear Guide for Sales Meetings

Now let’s double click into some of these steps. Here are a few of the strategies I find effective:

1. Before you even meet with the client, try to diagnose their needs, priorities, and budget. This will set you up for success in the meeting.

Aim to walk into the meeting with a solid understanding of the client’s needs. This will allow you to better understand the opportunities that exist within the company you’re selling to. Specifically, you should:

Learn the basics of the company: make sure to look at the company’s website, Crunchbase profile, and social media pages like LinkedIn, Youtube, and Twitter to understand the stage of growth and number of employees.

Assess the client’s strengths, problems, and pain points: take their products for a spin so you can understand the benefits and challenges first hand. Try to assess how your product could add value to what they’re already doing. If it’s a larger public company that you’re selling to, you should listen to their earnings call or read their investor relations report to learn about the company first-hand from its leadership.

Determine whether it would be beneficial to add a C-level team member in the meeting: as you grow, you can leverage the meeting opportunity to include a VP or C-level executive from your side. This might push the client to include an executive or ultimate decision maker from their side as well, making it easier to close the deal.

2. Set yourself up for success before a virtual meeting begins.

Test the Zoom or Google Meet settings 5 minutes before the call begins. Make sure to setup your tabs for the meeting and turn off all notifications on your phone. You should send a courtesy email with a reminder of the dial-in information. And finally, make sure to send any relevant documents or materials to attendees ahead of time.

3. Kickoff the meeting with introductions and take some time to connect personally with attendees.

It’s a good idea to hop on a little early and make small talk with attendees as they’re logging on. Having a good rapport with your clients can go a long way in relationship building.

Once everyone logs on, introduce yourself properly and let others on the call introduce themselves. You should quickly verify the end time of the meeting so you can pace the meeting appropriately.

From there, I advise going through the agenda and sharing your top-line goals with the clients. You should also inquire about any goals they might have for the meeting. This is an important step, but I wouldn’t spend more than 2-3 minutes in total on this. Then dive in!

4. Discover and learn by using the SPIN method to uncover what the client’s true needs are.

Now that you’ve learned as much information as possible about the client and their needs ahead of time, you can put your best foot forward in the meeting. I like to follow the SPIN method to lead a client meeting.

The acronym SPIN refers to the four types of questions that guide sales conversations: Situation, Problem, Implication and Need. You want to breeze through the S and P questions, and really focus on the I and N questions to get the most out of your meeting.

S: Situation Questions – these questions help you understand the basic facts around the client. In my experience, the questions that fall into this category add very little value to a meeting, and most of these questions can be answered in your own background research ahead of time. My advice is to spend as little time as possible here. Example of a situation question: “How many people do you have on your team?”

P: Problem Questions – rather than focusing on situation questions for a long time, you want to jump into problem questions as soon as possible. Problem questions probe clients on the challenges they’re facing in their day to day and with their current product solution, if they have one. You should be careful not to offend the client, in case they were the one who previously decided on the tool or service being used. Example of a problem question: “What are you missing most in your current solution? Does your current tool ever fail?”

I: Implication Questions – after assessing the problems the team is having, you can really dig into the implications and consequences of those problems on their business. This helps to demonstrate why they need to make a change. Example of an implication question: “What’s the productivity cost when the solution fails? ”

N: Need Questions – these questions are designed to uncover the core needs of the prospective client, the benefits they are looking for out of their next solution, and to guide the client to see the benefit of your product or service as a better solution. Example of a need question: “Wouldn’t it be simpler if the process were automated?”

5. Summarize the learnings and then dive into a demo to share information about your company.

Quickly read back what you heard from the client. Example of a read back: “To make sure that I captured your needs correctly, you are currently missing an automated solution?”

From there, it’s time to dive into your presentation of your company. Share your screen and give a demo to your clients, if possible. Throughout the demo, you can link back to the client’s needs. Example of this: “To your point that productivity costs are high, we believed in keeping costs low by [XYZ solution].”

It also helps to share use cases and case studies of other companies and how they found success with your product.

6. Leave time for answering the client’s questions and to do a proper close.

Summarize your findings and some key points. I find a three-point summary works great, but I try to never make it longer than three points.

Thank everyone for their time, and follow up on next steps. Try to have concrete next steps, and again, no more than three.

You should verify that all goals were met and that the clients don’t have any outstanding questions about the product. Log off the meeting (and make sure everything is logged off, like screen sharing).

7. Send a quick follow up note.

After a sales pitch, schedule a few minutes on your calendar to send follow up notes. I recommend make it a bit fun and memorable (i.e. add a picture of the meeting, or your team using the customer’s product…). Don’t let perfect be the enemy of good – timeliness matters, and it’s better to send a good follow up email quickly vs. a perfect follow up email a week later.

Make sure you also save some time to debrief with team members on your side to plan next steps.

In conclusion, you want to be prepared walking into a client meeting, and you should be extremely thoughtful on how you spend your time in the meeting itself. In part three of this series, we’ll dive deeper into how to craft the perfect sales pitch.

This is part two of a three part series on sales. Stay tuned for more!

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Building an effective sales strategy for startups: Part 1 – Mastering a customer-centric sales approach and outreach strategy

Pear’s Partner, Pepe Agell, learned the importance of mastering sales during his entrepreneurial journey with Chartboost, a mobile advertising company. Pepe led Chartboost and built sales and go-to-market strategy for the company from its earliest days to its acquisition by Zynga in 2021. He is now a Partner at Pear VC, based in Barcelona and focused on Pear Europe.

One of the biggest obstacles founders face early in their journeys is building a successful sales strategy. To take your company from 0 to 1 requires putting the customer at the center of what you do and building momentum in sales and product adoption. Whether they like it or not, founders are forced to wear a salesperson hat. To make their job easier, I’m excited to share a few of the lessons I learned over my decade leading sales for Chartboost.

1. Think about the Law of 250 to remember that each and every interaction with a prospective client is critical.

Joe Girard is acknowledged as the world’s greatest salesman, and he famously coined the Law of 250, which he believed to be the radius of influence for an average person.

The basic principle is that if you do a crummy job of selling your product, you could potentially lose 250 more customers. If you do a great job, you could potentially gain 250 more customers.

You might only get one shot to make an impression, so you have to prepare yourself for each and every interaction you have with a prospective customer.

2. Remember that HOW you sell is as much of a differentiator as WHAT you sell.

Founders focus on perfecting their product and service offerings for good reason – it’s critical to success. But, in my experience, founders often don’t carve out enough time for getting to know their target customers and crafting a sales strategy that reaches the right people in the right way.

The more you know about a client, the more leverage you have. The key to learning more is to research your clients, identify what they need to achieve, understand the impact your product or service can have on their business, and then engage your clients in a meaningful way.

3. Adopt a customer-centric sales approach every step of the way: don’t simply sell your products and features, sell the impact your product will have on helping your customer’s business improve.

Try to understand what is going on inside your client’s organization: What are their objectives? What are their obstacles? What stage of the journey are your clients on?

This can be easier said than done, so I like to break down this customer-centric sales approach into 4 buckets, which I call the 4 D’s:

Discovery: research and prepare for client interactions

Diagnose: identify where the areas of opportunity exist within the client’s organization

Design: create a proposal with the pitch tailored to the solutions your client needs

Deliver: clearly share your vision and close the deal

4. We operate in a social world. Put your best foot forward online.

First impressions matter. Your clients are very likely to look up your online profiles, so make sure you are building your online presence in a professional and clear way. Consider updating your LinkedIn profile with an updated photo (professional and smiling), a tagline or title that captures what you are passionate about, and share a clear blurb about your company story and what you’re trying to achieve. Put simply, don’t make a prospective client dig for information about what you’re selling, but rather make it easy to access and understand.

Establish contact with prospective clients. Don’t connect on LinkedIn blindly, but instead, send a quick note with context to make a connection. If you have a mutual contact with a strong connection with a potential client, you can ask for an introduction. Alternatively, you could just reach out and mention the common connection without directly asking that person for an introduction. These tactics boost the chances that the client will respond or accept your invitation to connect.

5. Be really thoughtful about how to structure your outbound messages and emails: aim to be clear, concise, and personal.

The shorter the email, the better. My rule of thumb is for a email to take no more than 30 seconds to read. If you can get your message across in 15 seconds, that’s even better.

In terms of what to say in the email, I suggest following the 3 R’s method to construct your outreach message:

Research: share more about what you learned in your research. Example: I can imagine you’re very busy right now with the success of your current [XYZ product] hitting the market.

Reference: reference an existing client or situation that relates to them, or something else. Example: We have several tools that might be helpful to you as you continue to scale [XYZ product] offering.

Request: state a clear request at the end: a meeting, a call, or whatever your hope to do. Example: Let me know if you are free tomorrow to discuss more.

6. Don’t overlook the importance of the sales meeting calendar invite. The invite itself is a powerful sales tool.

Once your client agrees to chat more, you have to get to work on making the best first impression. Creating a quality meeting invitation sets the tone for the meeting and creates brand awareness for your company. To put your best foot forward in the invite: state a goal of the meeting, add any relevant context, share any useful resources (example: a one pager of the product you’ll be pitching), include dial in information (and test out the dial in 5 minutes before the meeting begins), and include a backup phone number in case the dial in fails.

Your client may accept the invitation and add other team members to the invite. This will give you an opportunity to do some background research prior to the meeting to better understand who is on the team and who the decision makers in the room might be.

Carefully and thoughtfully compiling the invite will allow you to build brand awareness and create understanding and camaraderie, before even have your first meeting.

7. Prepare. Prepare. Prepare.

I’ve mentioned this already, but it’s worth underlining. I can’t emphasize enough the importance of preparation in the sales outreach process. You never want to wing an interaction with a client. The more you know about who you’re talking to, the clients vision and strategy, and the size of the opportunity, the more successful you’ll be.

In conclusion, these seven concrete steps can help you to become more customer-centric in your sales approach and outreach strategy. This is just the beginning of what you need to do to be successful on your sales journey.

In part two, you’ll build on the lessons you learned in part one, and we’ll move into the phase of the sales process where you’ll learn how to prepare for a customer meeting and effectively lead the meeting.

This is part one of a three part series on sales. Stay tuned for more!

If you’re interested in hearing more Pear news and seeing more posts like this, please subscribe in the footer below. We won’t spam you, and it’s easy to unsubscribe at anytime.

The Data and Analytics Playbook for Startups


Ali Baghshomali, former data analyst manager at Bird, hosted a talk with Pear on data and analytics for early stage founders. We wanted to share the key takeaways with you. You can watch the full talk here

While a lot has been said around building go to market and engineering teams, there’s not much tactical coverage for analytics teams. Yet analytics is one of the most fundamental and crucial functions in a startup as it launches and scales. 

When should you start seriously working on analytics?
Why should you work on analytics?
Who should you hire?
What should be in your analytics stack?
What are some case studies of company analytics operations?
What should you do moving forward?


When should you start seriously working on analytics? 

You should start thinking about your analytics platform when your company is nearing product launch. After your product is live, you’ll receive an influx of data (or at least some data) from customers and prospects, so you want to be prepared with the proper analytics infrastructure and team to make the most of this data to drive business growth. 

If you are just starting out and would benefit from working with analytics but don’t have much in house, consider using third party data sources, like census data. 

Why should you work on analytics? 

If done well, analytics will pay back many, many times over in time, work, money, and other resources saved as well as powerful insights uncovered that drive meaningful business growth. 

Who should you hire? 

In conversation, people often use “data scientist” and “data analyst” interchangeably. While fine for casual conversation, you should clearly understand and convey the difference when writing job postings, doing job interviews, hiring team members, and managing data teams. 

Data scientists work with predictive models through leveraging machine learning. Data analysts, in contrast, build dashboards to better display your data, analyze existing data to draw insights (not predictions), and build new tables to better organize existing data. 

For example, at Spotify, data scientists build models that recommend which songs you should listen to or add to particular playlists. Data analysts analyze data to answer questions like how many people are using the radio feature? At what frequency? 

Similarly, at Netflix, data scientists build models that power the recommendation engine, which shows you a curated dashboard of movies and TV shows you may like as soon as you log in. Data analysts would conduct data analysis to determine how long people spend on the homepage before choosing a show. 

Unless your core product is machine learning driven, you should first hire data analysts, not data scientists. In general, a good rule of thumb is to have a 3:1 ratio of data analysts to data scientists (for companies whose products are not machine learning driven). 

For early stage startups, stick to the core titles of data scientists and data analysts rather than overly specialized ones like business intelligence engineers because you’ll want someone with more flexibility and who is open and able to do a wider range of work. 

What should be in your analytics stack? 

Here are examples of tools in each part of the analytics stack and how you should evaluate options: 

  • Database: examples include BigQuery and Redshift. Analytics databases are essentially a republica of your product database but solely for analytics. In this way, you can do analytics faster without messing up product performance. In general, it is advisable to use the same database service as your cloud service. 
  • Business intelligence: examples include Looker and Tableau. Business intelligence tools help you visualize your data. They connect to your analytics database. You should pick a provider based on pricing, engineering stack compatibility, and team familiarity. Don’t just default to the most well known option. Really consider your unique needs. 
  • Product intelligence: examples include Mixpanel and Amplitude. Product intelligence tools are focused on the product itself, rather than the over business. Specifically, they are focused on the user journey. They get code snippets inserted from the product. Because they don’t encapsulate the full code, you should consider this data to be an estimate and use the insights drawn more directionally. Product intelligence tools can be used to create charts, funnels, and retention analyses, and they don’t need to be connected to other databases. 

What are some case studies of company analytics operations? 

Helping Hands Community is a COVID inspired initiative that services high risk and food insecure individuals during the pandemic. 

  • Team: 7 engineers, no data analysts
  • Product: basic with 1000 users
  • Stack: Google Cloud, Firebase for product database, BigQuery for analytics, Google Data Studio for business intelligence, and Google Analytics for product intelligence 

Bird is a last mile electric scooter rental service. 

  • Team: 50+ engineers, 30 analysts, 8 scientists, 6 analyst managers
  • Stack: AWS for cloud, Postgres (AWS) for product database, PrestoDB for analytics, Tableau and Mode for business intelligence, Mixpanel for product, Google Analytics for website, Alation for data, DataBricks for ETL, and Anodot for anomaly detection (you generally need anomaly detection when ~1 hour downtime makes a meaningful difference in your business) 

What should you do moving forward? 

Make a data roadmap just like you make business and product roadmaps. Data roadmaps are equally as important and transformative for your startup. List the top 5 questions you foresee having at each important point along this roadmap. Structure your data roadmap in a way that your stack and team addresses each of the questions at the point at which they’re asked. 

We hope this article has been helpful in laying the foundations for your analytics function. Ali is available to answer further questions regarding your analytics strategy, and he is providing analytics and data science consulting. You can find and reach him on LinkedIn here