Sales Foundations

Stop Blaming AI Agents for Low ROI If There’s No Traffic
Why AI Introductions and Human First Impressions Matter
Research (and likely your intuition) consistently remind us that first impressions have a massive impact on relationships, including workplace culture. A Princeton study found that people form impressions of others in less than one-tenth of a second. That’s faster than just about everything except the speed of light, sound waves and nerve impulses. These initial reactions, including judgments, are hard to change, and once locked in, they shape how we perceive someone's credibility, competence, and trustworthiness. In the (remote or in person) workplace, a well-handled introduction can increase team culture and productivity, while poor introductions can lead to confusion about who is doing what and nothing good comes from that lack of clarity.
Looking Under the AI Bridge, Why you should love your Trolls
Trolls have been part of the Internet since I can remember stumbling around user groups and dinosaur-aged chat programs (RIP AOL instant messenger), lurking in forums, comment sections, and social media feeds, sowing chaos and stirring controversy. The term “troll” originally referred to a fishing technique where bait was slowly dragged through the water to attract a bite. How does this look online? Baiting users into pointless arguments, negativity, or confusion. As the internet expanded and social networks of all shapes and sizes emerged, so too did an army of trolls.
The Future of AI is Billboards and Print Ads
We know that everyone won’t have a use case that requires a billboard, window sticker, bus ad, or flyer but a lot of people are still looking for tangible ways to be introduced to a business and between the SPAM, screen exhaustion, and good ol’ fashioned nostalgia of finding things as you explore we think there is a future here for offline marketing + AI.
Local Government Winning ⅛ of a loyal (AI) employee at a time
The future of work in government does not lie in replacing human employees with AI but in finding the right balance between human and AI capabilities. By hiring agentic AI as fractional employees, county governments can optimize their operations, deliver better services to their residents, and empower their human workforce to do what they do best—serve the community with creativity, empathy, and dedication.
Shocker: AI is not telepathic and it’s not really another tool
As artificial intelligence (AI) continues to become common place across workplaces regardless of industries, a common misconception has emerged: AI is often treated as just another tool, akin to legacy software-as-a-service (SaaS) platforms like CRM systems. Or, even worse, people expect AI to be magical in it's ability to immediately know everything or do anything. I'll focus on the former (legacy tools comparison and in the future tackle the do everything angle) Unlike traditional software tools, managing AI is more akin to managing a junior employee. This distinction is crucial for organizations to understand if they are to harness the full power of AI.
Hiring AI? You need to upgrade your job descriptions.
Job descriptions are often the first social contracts between a company and an employee. They provide clarity, define roles, and set expectations, serving as a blueprint for both employees and employers. As future-facing leaders start to hire artificial intelligence (AI) that works seamlessly with human colleagues and therefore creates hybrid teams, the need for clarifying job descriptions on who does what will become even more critical.
WW-AI-D: Focus on your competition not just your products and services to win
Understanding your product or service’s key benefits is essential. But, the most effective salespeople (AI or Human) don’t just stop at knowing what makes their offering valuable; they rock at differentiating these key points against their competition.
Question Everything with AI
Questions are fundamental to effective communication, guiding conversations, uncovering truths, and fostering authentic connections. In sales, the style and type of question a prospect chooses can significantly shift the response you need to give and the direction of the conversation. By understanding the various questioning styles, you (and now AI) can tailor your interactions to achieve specific objectives, whether in early qualifying conversations or end-of-sales-cycle chats where you are trying to close in on a purchasing decision.
Don’t Let Your Ex-Chatbot Ruin Your Current AI Relationship
Today’s chat experiences powered by AI are smarter, more intuitive, and, candidly, a lot more fun to chat with. So, let’s explore why it’s time to let go of your past chatbot traumas and embrace a more fulfilling AI relationship.
Can’t Google errr OpenAI Do That?
Throughout my earlier career days of the various tech booms I observed something wild yet consistent, entrepreneurs would often find themselves cornered by investors with a simple yet daunting question: “Why won’t Google just do this?”
Not Just a Pretty (Inter)face: Helping Venture Capital Investors See Beyond GPT Wrappers
One specific, and particularly annoying, phrase for entrepreneurs building specialized AI has gained traction: “GPT wrapper.” With thousands of AI tools now available, many of them on platforms like the OpenAI Marketplace, it's becoming increasingly common for applications to be built as wrappers around powerful language models like ChatGPT. These wrappers represent a significant portion of the AI market, providing interfaces that leverage the pre-trained capabilities of GPT models.
F SaaS but not literally, why the future may be less Vertical
The future of SaaS lies in leveraging the power of AI to transcend the limitations of industry-specific Vertical SaaS. By focusing on Functional SaaS, businesses can access flexible, scalable, and cost-effective solutions that provide deep industry context and customization. As AI continues to mature, it will bridge the gap between generalization and specialization, making Functional SaaS the preferred choice for organizations looking to optimize their operations and drive innovation. The shift from Vertical to Functional SaaS is not just a trend; it’s a strategic evolution that will define the next generation of software buyers and perhaps make it possible for little companies to act big and big companies to get nimble again.
Fine, don't hire AI but you should at least train one - your sales, marketing, and product teams will thank you
AI can play a transformative role, not just in product launches but in aligning teams and ensuring a consistent, accurate message across the board.
Why You Should Pay AI Commission, Not Just a Base (Subscription) Salary
At the risk of stating the obvious lets quickly frame up base salary vs commission et al. Think of base salary like a steady paycheck for showing up—it’s like paying rent every month whether you use all the rooms or not. But commission is more like getting a bonus every time you help sell something big—it’s like getting a slice of the pizza WHEN you bring a NEW pizza to the table. Other pay structures, like bonuses or profit-sharing, are more like dessert—you might get some after a great meal, but it’s not always guaranteed and if linked to broader company performance then it’s largely out of your control as an individual.
Capacity vs Capability: What are we really hiring AI for?
Before we get into the capacity vs capability discussion it’s probably worth saying up front that I am a salesperson (and the CEO of SkillBuilder.io). To put a finer point on it, I have been responsible for sales, sales teams, channels, partnerships, product launches, and everything in between (in addition to being a Chief Product Officer) for 20+ years. Why does this matter? Because most AI salespeople are being developed by a bunch of folks who have never held a quota and that matters.
Product Leaders
We at SkillBuilder understand that as a product leader, you are going to want to make sure the product information is absolutely accurate. When you have to choose between the information being compelling or accurate, and if you are the kind of product leader who is much more concerned with accuracy of the product information, then you are in the right place!
Sales Leaders
We understand that as a sales leader, you want to be both a chief storyteller and also be metrics driven while selling your product. We know that you feel accountable to the people under you doing the job of the outreach and the expectation of being on top of their game. So as a sales leader, SkillBuilder addresses your concerns by making sure that the answers and information you provide is up to date and accurate.
Founders & CEOs
We at SkillBuilder understand the issues you face as a new founder who have to deal with criticism, lack of belief and attention to the product, and self-doubts about the product not being perfect yet. The founder’s journey of struggling to bring something to market naturally comes with you facing a ton of questions!
Kloopify
Daniela and her team at Kloopify are pioneering the integration of sustainability into the procurement process, a crucial initiative in today's increasingly eco-conscious business landscape. As one of the earliest and most enthusiastic adopters of SkillBuilder.io, Kloopify has harnessed the platform's capabilities to streamline its operations, enhance team collaboration, and deliver impactful solutions that drive corporate sustainability.
Orita.ai
Founded by data scientists Daniel Brady and Zack Gow, along with seasoned DTC veteran, Aaron Schwartz, Orita.ai is been revolutionizing the email marketing landscape. The platform optimizes email lists by deleting spam accounts, removing duplicate IDs, suppressing unengaged contacts, and reactivating potential customers. To catalyze their growth and operations, the team at Orita.ai recognized the need for further optimization in their internal processes and turned to SkillBuilder.io.
The Forbes Funds
The partnership between Fred Brown's team at The Forbes Funds and SkillBuilder.io showcases a forward-thinking approach to leveraging AI technology to enhance organizational effectiveness and capacity building within the nonprofit sector. Their early adoption and active involvement in training SkillBuilder.io demonstrate a commitment to innovation and continuous improvement.
BlastPoint
Blastpoint provides customer intelligence and analytics solutions to sectors such as energy, finance, and automotive. The company has experienced rapid growth and has adopted an AI tool named SkillBuilder.io to enhance team collaboration, simplify messaging for non-technical customers, and develop sales collateral for industry events.‍BlastPoint's platform offers sophisticated ML and geospatial analytics, which, while powerful, were challenging to communicate to non-technical audiences. As the company grew, maintaining effective team collaboration and producing impactful sales collateral for frequent industry events became increasingly important.
Piper Creative
Cofounded by Aaron Watson and Hannah Phillips, Piper Creative is a cutting-edge video marketing agency that stands out for its innovative approach and practical service offerings. Specializing in video editing, production, and marketing strategy, they have a proven track record of producing thousands of podcast episodes, ads, and YouTube videos, garnering tangible insights and the best practices in digital marketing. 
Noire Distillery
Understanding that a cohesive narrative is essential in brand building, Kenyan employs SkillBuilder.io to ensure that his team is not merely workers but custodians of the distillery's story. With SkillBuilder.io, every team member becomes a storyteller, adept at sharing the rich tapestry of Noir's heritage, the meticulous journey of their handcrafted spirits, and the unique recipes that set them apart. This strategic alignment ensures that each narrative thread is woven consistently into the fabric of their brand, resonating with consumers and elevating the brand experience.
How To Train For The Stakeholder Gauntlet
It could be argued that the holy grail of product-market fit is having an employee who can pitch any prospective customer, and be entirely unfazed by the myriad job titles in attendance. COO, VP of Product, Head of PR, Sales Engineer, Data Science Lead… the more the merrier, and the more likely to move a deal forward. But at best, a typical company might have one all-star on the client side who can navigate this gauntlet of stakeholders in real-time.
The Known-Unknowns Of Competitive Differentiation
Spend enough time around product teams or Big 4 consulting firms, and you’ll inevitably find yourself using the Known-Unknowns Matrix in some capacity — especially when it comes to assessing your competitive differentiation in the market. I’ll spare you the full matrix walkthrough, and instead highlight its most actionable and operational quadrant: Known-Unknowns.‍
Why Is There No Department Of Differentiation?
If your org isn’t relentlessly differentiating itself from competitors and inaction, it’s running on borrowed time. Many legacy companies have found themselves in such a position, being disrupted by startups who are laser-focused on “why us, why now” — small, nimble teams who live and breathe differentiation. I’ll tell you where larger orgs go wrong in reacting to this challenge, and how to avoid being put on the defensive in the first place.‍
The ‘Challenger in Residence’ Is Your Org’s Missing Puzzle Piece - Meet CiR
Your Sales team? Your prospects? I’m going to tell you why the real answer is “nobody”, and how a new organizational perspective can change that answer to instill a sense of urgency within your customers.
Why FAQs Are The Greatest Test Of Your Company's Culture
If you want to know how unscalable culture festers in a company, look no further than their FAQs. Not the commoditized and sterilized list adorning the marketing website, but the list that swirls around the watercooler among employees who don’t see any differentiation in the business. I’m going to explain why those two lists don’t often line up, why it needs to change today, and how you can kickstart that change to build a resilient culture that breeds scale.

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