technology | lead up

b2b handshake on the left, college committee meeting on the right

B2B vs B2HE: They’re not the same

Selling products or services to colleges and universities might look a lot like classic B2B marketing at first glance, but the similarities are often only skin deep. Many vendors new to the space underestimate the real differences involved in business to higher education, which I like to call B2HE. Attempting to apply a standard B2B playbook to higher ed institutions can backfire, leading to longer sales cycles, disengaged stakeholders, and partnerships that fizz out before real value is delivered.

If higher ed is on your radar or you’re struggling to get traction there, understanding what sets B2HE apart is crucial. Here are some of the main reasons why selling to higher education isn’t just business as usual. Decision-making, budgets, values, and communication styles differ in B2HE.

Understanding the unique dynamics of B2HE

Why B2HE is more than just another vertical

Traditional B2B models are built around organizational efficiency and scale. But higher education operates on a completely different foundation, and it shows up at every stage of the buying process. There are a few key factors that set B2HE apart.

Navigating complex decision-making structures

Multiple stakeholders and diverse priorities

While most corporate deals are managed by a clear decision-maker such as a CIO or procurement director, higher ed purchases rarely rest in one person’s hands. Instead, you’re engaging an intricate web of:

Marketing, communications, and accessibility experts
Enrollment
Advancement
Budget and finance administrators
IT leadership and administrative officers
Department heads

Consensus is essential, requiring more meetings, more documentation, and a heightened focus on inclusive communication. This results in longer sales cycles, but also increases the likelihood of deeply buy-in when the decision finally lands.

Prepare for a slower, collaborative process that honors multiple voices. Treat conciseness and transparency as your most valuable assets.

Budget structures require adaptation

Funding, grants, and endowments

Budgets at colleges and universities aren’t structured like those at most private companies. They’re organized around fiscal calendars, government funding cycles, and multi-year endowment allocations. Subscription models tied to headcount or monthly usage may not resonate. Instead, higher ed buyers prefer:

Predictable annual costs
Multi-year contracts that provide budgeting stability
Transparent pricing that fits within allocated grant or state funds

Flexibility and predictability win over complexity.

Mission over metrics

Values are just as important as, if not more important than, ROI

Corporate buyers place heavy emphasis on ROI, scalability, and efficiency. Higher ed buyers still care about those, but just as often prioritize mission-driven outcomes like:

Student success
Community impact
Equity, diversity, and inclusion
Academic integrity and compliance

When selling to higher ed, your story has to go beyond efficiency. It must show how your product actually helps fulfill the core educational mission.

Learning platforms that improve accessibility or support underserved students instantly stand out, even if their ROI story isn’t the strongest on paper.

The demand for customization and flexibility

No size fits all

B2B vendors often seek scalable, repeatable solutions. But every college has its own legacy systems, departmental independence, and varying technical skills. This means your product needs to be:

Flexible enough to support unique workflows
Highly configurable for decentralized department ownership
Compatible with legacy IT infrastructures

Rigid, one-size-fits-all solutions rarely stick. Institutions expect partners to accommodate the idiosyncrasies that make their campus unique.

Offer product demos that highlight customization. Be ready to discuss integration with legacy data systems and non-technical user support.

Building enduring relationships

Focus on long-term partnership

A tech startup might swap vendors every two years in search of the next advantage. By contrast, higher ed institutions expect solutions to last and evolve. Once they invest in you, they want assurance that you’ll:

Provide high-touch, ongoing support
Offer comprehensive onboarding and training
Grow and adapt as their needs change

Expect more focus on references, trust-building, and post-sale relationship management.

Invest in a Customer Success program dedicated to higher ed. Highlight case studies that show long-term, evolving partnerships with other institutions.

Community and peer advocacy drive adoption

Peer recommendations make the difference

The higher education space is highly networked. Professionals regularly trade insights at conferences, on listservs, and through formal consortia. A peer endorsement from another university can carry more weight than any marketing collateral you might send.

Tactics to boost credibility in higher ed:

Encourage reference calls or campus visits among current and prospective customers
Support user groups and online communities
Invest in customer success stories specific to peer institutions

Word-of-mouth among institutions can either accelerate your adoption or stunt it completely.

Communication styles matter more than you think

Formality, context, and respect

Corporate sales outreach often favors brevity, casual tone, and friendly assumptions. Higher ed professionals value something quite different:

Clear, context-rich subject lines (e.g., “Supporting accessible learning at [Institution Name]”)
Well-written, respectful, and grammatically correct messages
Personalization and reference to the institution’s educational mission
Respectful timing and considered follow-ups

“Quick question?” subject lines and pushy weekly nudges don’t land here. Quality outshines quantity.

Develop tailored, thoughtful messages that acknowledge the institution’s specific goals and challenges. Assume your reader is analytical, busy, and invested in their work.

How to succeed in B2HE

Rethink your playbook

Treating higher ed like a standard B2B client almost guarantees you’ll miss the nuances that matter most. To stand out, you need to:

Rethink your sales cycle for consensus-based decisions
Structure contracts for stability and transparency
Develop messaging tailored to mission-driven priorities
Feature solutions that are adaptable, configurable, and legacy-friendly
Build long-term, trust-driven relationships
Leverage peer advocacy and customer-led storytelling
Communicate with clarity, respect, and context

By truly understanding and adapting to the B2HE model, you position your company as a valued partner rather than just another vendor. That mindset shift will pay off in longer, richer relationships and stronger results for the institutions shaping our future.

Wrap-up

Unlocking higher ed as a growth channel isn’t about changing what you sell. It’s about honoring who you’re selling to and how they define success. Start by reevaluating your messaging, your pricing structures, and your approach to ongoing support. Listen closely to current customers and ask for feedback on your outreach style. Engage with the broader higher ed community and invest in building references and relationships.

If your solution supports educational missions and you’re ready to rethink your approach, the B2HE world can offer uniquely rewarding partnerships that last a decade or more.

Looking at constraints as a positive

Most people see constraints as obstacles to overcome. But what if your biggest limitations might actually be your greatest opportunities for breakthrough thinking and meaningful progress?

When resources are scarce, deadlines are tight, and options feel limited, our natural instinct is to focus on what we can’t do. We get stuck in frustration mode, wishing we had more time, more budget, more resources, or more freedom. But this mindset misses a fundamental truth: constraints don’t just limit us. They can actually be liberating.

Hear me out.

Don’t underestimate the power of limitations

Constraints force us to think differently. They strip away the paralysis of infinite options and demand focus on what truly matters. When you can’t do everything, you’re forced to do the right things really well.

Consider the most innovative solutions you’ve encountered. Chances are, many emerged not in spite of constraints, but because of them. Look at all the innovations and pivots that happened during COVID!

Take Georgia State University, for example. When in-person orientation was canceled during COVID lockdowns, they didn’t try to replicate the traditional experience with clunky Zoom calls. Instead, they launched a gamified digital orientation that used mobile apps, behavioral nudges, and personalized messaging to walk students through everything from class registration to financial aid. Not only did engagement increase, but the infrastructure they built continues to support hybrid orientation year-round. The constraint became a springboard for deeper personalization and better outcomes.

Or look at Little Sesame, a Mediterranean fast-casual restaurant in Washington, D.C. When they had to shut their doors, they could’ve waited it out. But instead, they pivoted to launch “Hummus at Home” meal kits, a creative way to bring their brand into customers’ homes. They paired that with a community initiative called “Feed the People,” delivering free meals to frontline workers and local families. In the process, they built a new revenue stream, expanded their customer base, and deepened their brand’s emotional resonance.

These are perfect examples of how constraints can channel creative energy into focused, high-impact solutions. When limitations demand better thinking, organizations often uncover approaches they wouldn’t have considered in times of abundance.

How constraints may foster better thinking

When facing unlimited options, we often freeze. Research shows that too many choices can lead to decision fatigue and decreased satisfaction. Constraints narrow our focus to what’s actually possible and important.

With limited resources, you can’t pursue every good idea. Instead, you must identify what matters most. This forced prioritization often reveals insights that would remain hidden in environments with excess.

Constraints make us more creative with what we have. When the usual solutions aren’t available, we’re pushed to find novel approaches, repurpose existing resources, or discover efficiencies we never knew existed.

Shifting Your Constraint Mindset

The key to leveraging constraints isn’t to pretend they don’t exist or to simply “think positive.” It’s to fundamentally shift how you relate to them.

“I Can’t” -> “How Might I?”

Instead of focusing on what constraints prevent, ask what they make possible. What new approaches do they open up? What assumptions do they force you to challenge?

Problem -> Parameter

Treat constraints as design parameters rather than problems to solve. If you’re building a house, the lot size isn’t a problem—it’s a boundary that shapes your design. Apply the same thinking to your professional limitations.

Scarcity -> Focus

Reframe limited resources as focused resources. When you can’t do everything, you get the rare chance to do the right things exceptionally well.

How you talk about constraints matters.

In my post “Venting: The Not-So-Silent Culture Killer”, I explored how habitual complaining creates a ripple effect of powerlessness. When we vent about constraints without reframing them, we reinforce the idea that we’re stuck. But when we treat constraints as catalysts, we reclaim the narrative and the power.

Getting started

Embrace “good enough”: Perfectionism and constraints rarely coexist. Often, a good-enough solution delivered on time and within budget is far more valuable than a perfect one that’s too expensive or too late.

Look for unconventional resources: When traditional resources are limited, think creatively. Can you partner with another team? Leverage user-generated content? Build a minimum viable version first? Let your constraint spark resourcefulness.

Question assumptions: Constraints surface hidden assumptions. Use them as prompts to challenge standard approaches and uncover new paths.

Use and build on what you have: Inventory what’s already working. Often, progress comes not from acquiring more, but from better using what you already have.

Even in the most constrained situations, you retain control over your response. You can’t always change your circumstances, but you can change how you approach them.

As noted in “Developing Resilience in the Face of Adversity”, focusing on your locus of control is essential to both personal effectiveness and professional impact. When you shift from lamenting constraints to leveraging them, you unlock a form of agency that’s deeply energizing.

When a constraint shows up, pause before defaulting to frustration. Ask:

What does this limitation force me to focus on?
What creative solutions does this constraint make necessary?
How might this restriction lead to a better outcome?

Keep a record of times when limitations actually led to better solutions. This helps build confidence that the next constraint could be a new opportunity.

And when you see colleagues struggling with limitations, share your own constraint-to-clarity stories. This builds a culture that sees possibility where others see barriers.

What about you? When have you benefitted from a constraint?

8 creative ways to use ChatGPT to save time

When someone asks us “how are you?,” the common answer is “busy”. Yes, we’re all busy and never seem to have enough time. Over the last year, I’ve discovered that one of the best time-saving tools isn’t a scheduling app or productivity hack, but ChatGPT.

While most people know ChatGPT can write emails and summarize documents, some of the most powerful time-saving benefits come from more unexpected, creative uses. Here are some ways I’ve used ChatGPT to get more done faster.

Parse notes into action items

I love using Attention as my AI-powered notetaker, but sometimes I skip it. People can be more open when they’re not being recorded, and I still enjoy manual note-taking for retention.

Still, I often end up with messy shorthand in my Remarkable or Notes app. I’ll paste the text into ChatGPT and ask it to turn it into an action plan with tasks, deadlines, and priorities.

Example prompt:
“Here are my notes from today’s team meeting. Can you create a prioritized task list with deadlines and owners?”

Brainstorm faster

“I write because I don’t know what I think until I read what I say” is a quote by Flannery O’Connor that I can relate to. Whether it’s working on a new feature or product idea, piece of content or song, or I am looking for new initiatives for the company, I start jotting down anything that comes to mind without internal censorship. When you’re stuck in idea limbo, whether it’s for marketing copy or an outside-of-the-box solution to a problem, ChatGPT can jumpstart your brainstorming. Just give it context and ask for 10 ideas to kick it off, which can help you avoid the dreaded blank page and gets your creative juices flowing faster.

Example prompt:
“I’m launching a new feature for higher ed web teams. What are 10 creative blog post titles that balance approachability and professionalism?”

Simplify complex concepts for yourself and others

Whether you’re learning something new or explaining a technical concept to someone less familiar, ChatGPT can help summarize jargon-heavy material in plain English. For example, if someone asks what a specific section in a legal contract means or looking to understand a highly technical concept, you can ask the tool to break it down in simpler terms. In fact, ChatGPT is usually pretty good at coming up with relatable analogies. I recommend being as specific as possible in defining who the intended audience is.

Example prompt:
“Explain this section of a SaaS contract in plain English for someone with no technical or legal background.”

Create first drafts

From RFP answers to project requirements, the first draft is often the most time-consuming. I use ChatGPT to write a rough outline or narrative based on key points. Editing from a starting point is so much faster than starting cold. For things like Statements of Work, you can even create your own custom ChatGPT by teaching it about what you’re looking for and uploading existing SOWs (minus the customer name) to use as guidelines.

Example prompt:
“Based on these bullets, draft the first two paragraphs of proposal for an implementation project.”

Prepare for conversations

Before heading into a call with a potential partner or customer, consider asking ChatGPT to help prep questions, review context, or suggest talking points based on previous interactions or public info. It saves me from digging through inboxes or LinkedIn for background, although, admittedly, sometimes I can’t help it.

Example prompt:
“Help me prepare for a call with [customer/partner] interested in [topic]. Summarize the top 3 news stories from the past 6 months about [Customer Name] and highlight anything relevant to digital transformation or leadership changes.”

Create new templates or formats

One of the most underestimated time-saving superpowers of ChatGPT is its ability to build custom frameworks, templates, and models on the fly, which is especially helpful when you’re tackling something ambiguous or complex.

Whether you’re evaluating vendors, planning a new campaign, scoping a project, or making a strategic decision, having the right framework helps you move faster and with more clarity. But instead of spending hours on the internet for one that almost fits your needs, ChatGPT can help you create one that’s tailored to your situation. The trick is to not settle for the first answer the tool gives you, but to keep asking for refinements until you have something that is a great starting-off point.

Example prompts:

“Build a scoring matrix for whether or not to RFPs based on fit, scope, risk, and competitive positioning.”

“Create a content planning template based on the awareness, consideration, and decision stages of the buyer journey.”

“Develop a Standard Operating Procedure template for customer onboarding.”

Develop learning plans

This is one of my favorite use cases. When I want to sharpen my skills and acquire more knowledge about a certain area, I ask ChatGPT for learning plans based on my time frame and availability.

Example prompt:

“I want to learn more about GDPR and how it affects web content and web personalization. Create a two week crash course for me with relevant resources like articles, videos, and podcasts. I can spend 15 minutes a day on this”

Use it as a sounding board

Sometimes you just need a gut check on tone, clarity, or how something might resonate better with your audience. ChatGPT is great for quick, low-stakes feedback that helps you keep moving. Whether I’m drafting an email that needs to be direct but diplomatic, or tweaking a copy that just doesn’t seem to hit the note I’m aiming for, I’ll often paste it in and ask for suggestions or a tone check. It’s like having a neutral second set of eyes without needing to bug a colleague.

That said, I draw a line when the context is deeply emotional, politically sensitive, or calls for real empathy. In those cases, I still rely on my own judgment or talk it through with someone I trust. For me, ChatGPT is less about replacing human insight and more about accelerating the mechanical parts, so I have more time and mental space for the conversations that actually require the human touch.

Example prompt:
“Does this message sound too unempathetic? I want it to be clear and firm, but still respectful.”

What about you? What are some ways in which you’re using ChatGPT to save time?

Supercharging Customer Success: how AI lets you do more of what matters

From strategic advisor to renewal champion, from ad hoc support provider to educator, and empathetic ear, as a Customer Success Manager (CSM) you often wear many hats. In a role where responsiveness and proactive engagement are crucial, time is your most precious asset. That’s why ChatGPT and other AI tools can be transformative in increasing productivity and impact, as they can free up a significant amount of time, so that the CMSs can focus on providing maximum value to their clients.

Here are some ways in which CSMs can use AI, particularly ChatGPT (along with a few shoutouts to other tools) to stay ahead and organized and provide personal service and attention without losing their minds.

Prepare for customer calls

Every CSM worth their salt spends a good amount of time reviewing a customer’s account prior to a meeting with them. This includes renewal dates and amounts, usage data, and, most importantly, reviewing the activity history and summaries from past meetings. ChatGPT can come in handy when it comes to synthesizing the information and creating an agenda prior to reaching out to set a customer call. A sample prompt: “Based on the summaries of the last four meetings with this client, create a three-point agenda focused on new users, feature adoption, and potential Services project.”

In addition, you can use ChatGPT to gather pertinent information about the customer that may not be directly related to your product or services. For example, you could ask it to identify a couple of newsworthy items, detect policies, industry changes or events that could affect the customer, or get a summary of the customer’s high level strategies.

A couple of ideas for prompts:

“Summarize the top 3 news stories from the past 6 months about [Customer Name] and highlight anything relevant to digital transformation or leadership changes.”

“Here’s [Customer Name]’s 2025 strategic plan. Extract the top 5 goals and suggest how our platform could align with each?”

A quick word of caution: watch for potential pitfalls like hallucinations or misinterpretation, particularly when summarizing nuanced meeting content.

Turn meeting notes into follow-ups

If you don’t already have an AI tool to automatically join your calls and provide notes afterwards (we do, but I still prefer to take notes manually with my Remarkable and then convert them to text), ChatGPT is great at rewriting notes and organizing them into action items. It also makes it a breeze to send follow-up emails. Simply ask: “Turn these meeting notes into a summary email for the client, with clear action items and deadlines.” Use the time you save to handle the action items and tasks assigned to you. If your meeting was extensive and included a number of different stakeholders, you can even ask the tool to write separate, personalized emails based on each person’s or group’s priorities, challenges, questions, and interests.

Create customer-facing resources

You probably have a plethora of resources available that you can share with customers, whether that’s white papers, your knowledge base site, product documentation, pricing sheets, or marketing one-pagers. But sometimes, your customer needs something more custom, which is where ChatGPT (and other tools, such as Google’s NotebookLM) can come to the rescue. A simple example: You have a customer who has been remiss in updating their software, so now they are a few versions behind. They ask you to give them a summary of the most important features and security enhancements that have been implemented since the last time they upgraded. Instead of combing through pages of release notes, you can simply copy the URLs of the notes and ask ChatGPT: “Summarize the key features of these releases, specifically as they pertain to security and usability. Put them in chronological order and add the benefits of each new feature.” Or you can ask the tool to eliminate jargon and simplify an array of rather technical articles into a summary for non-technical users.

Make tailored communication scalable

In order for you to serve all of your customers in a highly personalized way, it’s important that you have time to do so, and that, as counterintuitive as it may sound, involves making communication more scalable. For example, you may start an outreach campaign for selected customers in order to tell them about a set of features that they don’t seem to be using. You can have ChatGPT craft a few different versions of our email depending on their profile (number of users, SaaS versus on-prem customers, or industries. Similarly, you can use ChatGPT to plan quarterly business reviews for customers that are similar to each other based on the aforementioned criteria. This approach will make it easier for you to detect patterns, too. Here is an example prompt: “Write an email to our customers in finance to offer a QBR in which we discuss how [our product] has helped them with [initiative/goal] and discuss if and how [change in the industry] will affect them. Make the tone professional but friendly.”

Highlight proactive insights

ChatGPT can even process usage metrics and support ticket data. Simply upload your data from Mixpanel, Hotjar, Amplitude or whichever tool you have in place and ask it to provide insights for you to use in your next meeting with the customer. Those could be red flags (for instance if the customer is not using a large percentage of features, or you see declining logins) or potentially areas for expansion. A sample prompt: “Analyze this summary of [Customer Name]’s usage and tell me about trends I should ask about in my next meeting with them”. If you have a fantastic support team (like we do at Hannon Hill), you can also upload support tickets and summaries over a certain time frame and show your customers how (and how quickly) you’ve helped them or helped their end users.

Facilitate internal collaboration

As I mentioned in one of my previous posts, there’s no such thing as over-communicating when it comes to your customers. I am a firm believer in keeping team members from every team in the loop. But not everybody has time to read multiple paragraphs of meeting recaps or long threads of emails. Use ChatGPT to create the right types of information for the right audience in the right channels.

A few examples:

“Summarize the transcript of this meeting into a Slack message for the product team that breaks the customer’s feedback down into: wishlist, complaints, and praise.”

“Draft a CSM onboarding brief for a new team member taking over the [Customer Name] account. Include company overview, implementation status, desired outcomes, success metrics, key stakeholders, risk factors, and next steps.”

“Summarize the latest renewal conversation with [Customer Name] for internal tracking. Include renewal likelihood, objections or blockers, contract value, timing, decision-maker insights, and follow-up actions.”

Using ChatGPT or other AI tools is not a replacement for highly personalized, high value interactions with your customers. It should free you up to do more of what matters because AI can be your bionic arm to help you be more efficient, reduce the busy work, and do things that AI is just better at than humans are, which is processing large amounts of data. The goal is for you as the CSM to drive value, build loyalty, and be a highly valuable partner.

What about you? What are your tips for CSMs when it comes to using ChatGPT?

Why I talk to customers all the time (even though I “have a company to run”)

This is a topic that has come up frequently at our company and in my professional network. There’s a common idea that once you’re in a leadership role, especially as a CEO, you should operate ‘at a higher level.’ Meeting with customers? That’s seen as working in the business, not on it. You need to be focused on strategy, scale, and the big picture. Why would you be in the weeds with customers? Truth is that I talk to customers all the time and I will continue to do so.

Yes, we have an amazing Success team, and they have interactions with customers every day. And it’s also true that I have to focus on running the company. But meeting with customers is a vital part of my job. After all, they use our products every day.

Customers keep you grounded in reality

You can look at dashboards and metrics all day long, but nothing gives you clarity like a 30-minute conversation with a client who is trying to solve a real problem with your product. We’re fortunate that our customers are blunt and can be counted on to share with us what’s working, what’s challenging, and what they wish they could do in the system, but aren’t able to. And while we have an Idea Exchange, sometimes, users are having a hard time articulating their goals, or they think that it’s on them to spec out certain features, when in reality, all they need to do is articulate what they’re looking to accomplish. That’s when having conversations with them is powerful and invaluable. Those conversations are also a humbling reminder of the impact that our products have. In addition, hearing first hand how recent events, including policy changes and the economic climate, are impacting their world, helps us serve our customers in a more focused and intentional way.

It’s not about micromanaging

It’s inevitable that when you talk to customers as much as I do, the word “micromanaging” will be thrown around, so let’s be clear. I’m not stepping in to “fix” anything or take over someone else’s role.
I’m there to learn. And sometimes, to connect dots between what I hear in a customer meeting and what I see in a product roadmap, a team challenge, or a strategic decision we’re making. When you only see your customers through aggregated feedback or secondhand reports, it’s easy to miss the nuance.

It’s about relationships

Some of the best product ideas we’ve launched started as a casual comment on a customer call. Some of our most loyal champions came from open, honest conversations about what wasn’t working. Those are conversations that could have easily been avoided but instead became a foundation for trust.

Especially in higher ed, where roles are evolving, budgets are tight, and teams wear multiple hats, building those relationships isn’t just helpful, but it’s essential. We’re not solving generic software problems. We’re helping real people support their institutions in complex, changing environments.

There’s a lot of talk about “finding your why”, and in most cases, this includes your family, being a great example to your kids, or wanting to change your industry (and sometimes the world). Meeting with customers can add to your “why”, when you establish a deep connection to their raison d’être.

It’s how you make better decisions

Every time I talk to a customer, I get more context for the decisions we make as a company.

It’s easier to prioritize when you’re not guessing. It’s easier to advocate for your team when you can speak directly to how their work impacts real people. And it’s easier to say no to distractions when you’re reminded, firsthand, of what your customers actually care about.

“Too busy” isn’t a badge of honor

Some leaders pride themselves on being unreachable. That’s fair. It’s just not my preference. If the people using our product are willing to give us their time and trust, the least I can do is make space for that, especially when their insights help us grow in the right direction.

Talking to customers isn’t a distraction from running the company, but a critical part of it.
The further removed you get from the people you serve, the more likely you are to make decisions that look good on paper—but fall flat in real life.

So yes, I talk to customers. Because I have a company to run.

What about you? How often do you have direct interactions with your customers?