The Founder's Guide to Sales: Tools and Tactics to Grow Without Burning Out

Selling your product or service shouldn’t require a personality transplant. But for many founders, the sales process feels uncomfortable, overwhelming, or downright unnatural. Whether you’re sending the first invoice, raising your prices, or figuring out how to follow up without feeling pushy, sales is where strategy and self-doubt often collide.

That’s why we hosted The Founder’s Guide to Sales, a conversation focused on making the sales process more strategic and less stressful. We were joined by two leaders who bring hands-on experience building and scaling sales strategies that drive real results. We unpacked what it really takes to build a sales system that feels clear, consistent, and human.

Clarify Your Message and Offer

Before you can sell confidently, you have to be able to talk about what you do in a way that makes sense, to you and to your customers. But when you’re so close to your work, it’s easy to overcomplicate things. You start adding too much context, over-explaining the details, or second-guessing if you’re saying the “right” thing.

When your offer isn’t clear, it doesn’t just confuse your audience it creates friction for you, too. You hesitate to promote it, struggle to price it, and walk into every sales conversation wondering if it’s landing. That’s why clarity in your messaging isn’t just about saying the right thing, it’s about saying it with confidence.

To build that confidence, start by:

• Write down what you do in one or two sentences. If someone lands on your site or hears your pitch, will they immediately understand who you help and how?

  
  

• Spot the gaps. If your offer requires too much explanation, or if people are regularly confused about what you do, it’s time to simplify.

• Pressure-test your message across the sales cycle. From intro email to final pitch, your message should stay consistent and clear at every touchpoint.

• Say it out loud. Confidence is built through repetition. Practice talking about your offer until it feels natural.

Pricing With Clarity and Confidence

Pricing tends to be where emotion and logic often clash. For some, the fear is charging too much. For others, it’s charging too little. But in both cases, the tension comes back to the same thing: not being grounded in your value.

Start with the outcome. What changes for your customer after working with you or using your product? Use that transformation as your anchor, not just competitor benchmarks. Then test and adapt. If people hesitate, ask why. If they say yes quickly, ask what clicked. Each conversation is a data point that gives you the clues to refine how you position, price, and package your offer.

From Interest to Action

Most sales don’t happen on the first conversation. And even when someone seems excited about what you offer, that interest can quickly fade if you don’t have a plan for what happens next. A lot of business owners worry about coming off as too “salesy,” so they hold back. They avoid the follow-up, skip the reminder, or let conversations just fizzle out.

But having a thoughtful follow-up process isn’t pushy. It shows that you’re invested and that you care enough to keep the conversation going. The key is approaching it with empathy and intention. Every prospective customer is navigating their own timeline, priorities, and hesitations. So instead of defaulting to silence when someone doesn’t immediately say yes, start thinking of the follow-up as an invitation.

Instead of sending a generic “Just checking in!” message, try asking yourself:

• What’s still unclear? Re-share your offer or key benefits in simpler terms.

  
  

• What reassurance might they need? Send a testimonial or example of past results.

  
  

• Are they stuck on logistics? Offer a breakdown of your process, pricing, or next steps.

  
  

• Do they need more time? Ask if they’d like to revisit the conversation later. Then actually schedule it.

Build a Sales System That Grows With You

You land a sale and now it’s time to celebrate. But then what? Next time it’s a new lead, a new follow-up, and your mental energy is already spent. After a while, it starts to feel like the wins are random and you’re just running yourself into the ground trying to keep up.

If that sounds familiar, you’re not alone. For a lot of business owners, sales is less of a system and more of a scramble. But once you’ve got proof that people want what you’re selling, it’s time to build something repeatable. A system doesn’t have to mean software or automation. It just means putting the right checkpoints in place to help you stay consistent, stay organized, and scale your effort without burning out.

Practical Ways to Start Systemizing

• Map your sales cycle. Write out the typical steps someone takes from first contact to final payment. What’s happening at each stage? What do you send, say, or share?

• Templatize your common messages. Save versions of your intro emails, DMs, proposals, and follow-ups so you’re not reinventing the wheel every time.

• Track your pipeline. Use a tool like Notion, Trello, or Airtable to keep tabs on who’s inquiring, who you’ve followed up with, and what stage they’re in. Even a whiteboard or spreadsheet works.

  
  

• Identify what you need to stay consistent. Is it a calendar reminder? A check-in every Friday? A designated follow-up day each week? Pick one simple habit that helps you stay on top of your leads.

Keep It Moving

There’s no one-size-fits-all formula for sales. But what does work is staying grounded in your message, getting clear on your offer, and building systems that support your consistency, not just your next close. Remember, it doesn’t have to be perfect. It just has to keep moving.

Want to dive deeper? Download our free Simple Sales Worksheet to get clear on your offer, map out your process, and start building a sales strategy that actually works for you.

About the Panelists

Lynn Greenberg is the Founder and CEO of Pivt, the leading platform turning career transitions into engines of retention and loyalty through peer connection. By pairing employees with peers who understand their journey and supporting them with AI-powered smart matching. The result is uncertainty transformed into belonging, and belonging into stronger teams with measurable business impact. Recognized by Forbes 30 Under 30 (2022) and Forbes Next 1000 (2021), Lynn also serves on the Board of Trustees at Franklin & Marshall College, where she champions initiatives that empower the next generation of leaders. Before founding Pivt, Lynn gained experience at Bloomberg LP in London and Autonomy Ventures, where she specialized in startup deal flow, team management, and portfolio growth. Today, she pays it forward as a mentor and advisor through Women in Business at Yeshiva University, Astia Angels, and London & Partners. Lynn is a frequent speaker on the future of work, belonging, and employee well-being, with engagements at SXSW, Harvard University, NYU Stern, Columbia Business School, Oxford University, Brandeis University, and the NY Venture Summit. Her thought leadership has been featured in Forbes, The London Evening Standard, and Digital Trends, with contributions to Thrive Global, ERC Worldwide Mobility Magazine, Startup Magazine, and the Entrepreneur Podcast Network. 

Scott Loft is an industry veteran with more than 30 years of professional sports leadership experience in the NFL, NHL and NBA. Loft joined the Thunder in 2010 and is responsible for the Thunder’s overall strategy and tactics for all ticket sales, retention, database operations and business intelligence including season ticket sales, group ticket sales, executive suites and Club Level memberships. His sports career started with the NBA’s Philadelphia 76ers, where he spent nine seasons, culminating as the director of ticket sales. After, Loft became one of the first employees with the NHL’s expansion Nashville Predators, where his ticket sales team became the first NHL or NBA franchise to qualify for expansion by selling more than 12,000 season tickets before the NHL franchise was awarded to the city of Nashville. After five seasons, Loft joined the NFL’s Jacksonville Jaguars as executive director of ticket sales and marketing. His five years were highlighted by the local oversight of the ticketing functions for Super Bowl XXXIX, which was played in Jacksonville in 2005. Loft then continued his NFL career with the Miami Dolphins, where he stayed until he joined the Thunder. Prior to his career in sports, Loft received his undergraduate degree from Ball State University in Muncie, Indiana, and his master’s degree from Temple University in Philadelphia.

Simple Sales Worksheet.

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