Sharpend

I work with startup founders to develop self-awareness, improve emotional intelligence (EQ), learn communication/leadership skills and scale with their business.

Prior to coaching I spent 7 years as founder and head of marketing at Looksharp, and then worked as a marketing executive and advisor to a number of leading San Francisco startups. 

Learn more at https://www.sharpend.co/

Executive Coach

500 Startups

Mentor

Parallel18

Various Companies

Advise, consult, and do marketing work for various venture backed startups.  

Specialties include:
-SEO
-Content Strategy
-Content Development
-Marketing Ops (automation through sale)
-Lead Generation 
-Business Development
-Data and Analytics
-Email Marketing
-PR and Marketing Communications
-Brand Strategy & Creative

Software Expertise includes:
-Google Analytics
-SQL
-Marketo
-Salesforce
-ExactTarget
-Mailchimp
-Optimizely
-SproutSocial
-Trello
-more

Marketer in Residence

Carta

Helped Carta through a critical rebrand, new marketing team hires and growth of demand gen channels that resulted in a 40% lift of net new MQLs.

Demand Generation:
-Managed Carta's inbound marketing efforts including webinars, white papers, and product marketing content. Webinars alone accounted for a 20% increase in monthly marketing generated revenues.
-Collaborated with Carta engineering team to implement site-wide SEO changes that resulted in numerous keywords moving from 50+ rankings into top 3 results and a 70%+ increase in organic traffic.
-Developed and launched Carta's first-ever event marketing series including two large-scale half-day events in New York and San Francisco. Each event was cash-flow positive and resulted in hundreds of net new leads, increased brand exposure and powerful online content.
-Worked closely with Carta's outbound email team to nurture new leads from lead generation through the sales pipeline.

Rebrand:
-Helped develop new brand messaging map, including key messages for press, current customers, internal stakeholders and more.
-Worked with engineering team to develop strategy for domain cutover and technical rebrand implementation.
-Collaborated with marketing, engineering, and design team to help redesign and rewrite content for every webpage on the Carta website and reposition product pages with new brand in mind.

Team:
-Hired and grew marketing team from 1 to 6 people. Led charge in interviewing, hiring and training new marketing hires.
-Used Asana to manage team goals and sync day-to-day work with broader business strategy.
-Developed marketing dashboards and pulled key marketing metrics using SQL, Google Analytics, Looker, and other tools.
-Presented marketing metrics at monthly KPI and leadership team meetings.

Digital Marketing

Looksharp

Founded Looksharp and led the marketing team from idea stage through Series A and beyond. Used an "Iterative Marketing" approach (running rapid fire tests and using data to track and scale campaigns) to drive user and revenue growth.

Overall:
-Grew student audience from 0 to over 10 million uniques annually through SEO, business development, content, press and more.
-Generated over 100,000 inbound B2B leads to support successful sales operation.
-Built reports using SQL and Google Analytics to measure campaigns and drive business strategy.

SEO:
-Worked with engineering and design team to optimize website and gain #1 ranking for over 90% of top keywords in the internship space.
-Developed content strategy and managed team of fifty plus writers to support SEO goals. 
-Used Optimizely to improve conversion rate on SEO landing page by over 50%. 

Content:
-Developed long term content strategy using personas, competitive positioning, and SWAT analysis.
-Managed editorial team of 50+ bloggers to create compelling daily content.
-Invented new recurring B2B content including 'Annual Internship Report' to monthly "College Hiring Webinars" and more that drove thousands of net new leads.

Data​:
-Queried SQL database to develop monthly cohort graphs used to analyze business KPIs.
-Queried Salesforce and Marketo to pull reports and graphs and analyze marketing / sales operation.

Branding and PR
-Developed relationships with top industry journalists and received press mentions in publications including: the WSJ, TechCrunch, WashingtonPost, Mashable and more.
-Managed brand transition from established brand to a parent brand including a number of technically challenging changes.

Founder

Founder -> CMO -> Exec Coach

I coach founders and co-founders from Series B - D. I specialize in co-founder dynamics--helping co-founders build more effective and fulfilling partnerships. 

I believe in a world where leaders have done the work to know themselves, in order to build lasting businesses and a more interesting future.

Nathan Parcells

I'm a co-founder & CEO of Schematic -- an entitlements and monetization platform built on top of Stripe Billing. 

Our thesis is that AI transforms B2B monetization. 

SaaS monetization was static & seat-based. 

AI monetization is hybrid pricing & hybrid selling across multi-product offerings. 

Developers shouldn't have to reinvent the wheel when it comes to implementing & maintaining pricing & packaging. Product & growth folks should be able to control and iterate on monetization without code changes. They should be able to operate with speed and easily align their product roadmaps with continuous pricing & packaging releases. 

The future of monetization looks far more like telecoms in the 90’s than SaaS in the 2010's.

Enough about that.

As a kid, I wanted to play professional soccer, and I pursued that into my early 20’s, playing collegiately & then semi-professionally. 

My professional journey off the field began with a community visioning campaign to help continue Chattanooga TN’s revitalization, then a short, but formative stint with an edtech startup, which got me interested in startups, and then a year at a fund of hedge funds, before founding my first company in 2012, RootsRated.

Founding RootsRated kicked off what has now been a 15-year journey into building startups. RootsRated began as a go-to site for outdoor recreation and adventure travel. We later pivoted to SaaS, launched Matcha, a content marketing platform, and eventually, were acquired by Springbot, an email marketing service. 

After Matcha, I joined Automox, a leading ITOps platform, where I wore multiple hats—Director of Growth, Chief of Staff, and VP of Ops. Among other things, I led pricing at Automox, which led to the founding of Schematic. 

I grew up in Chattanooga, spent the last ~7 years in Atlanta which is one of the great cities, and recently moved to Colorado with my wife, two kids, and two dogs. Attended the University of Richmond, captained the soccer team, and studied International Relations & French (though my French has since atrophied). 

Outside of work, I enjoy trail running and becoming a cycling addict. Occasionally share my thoughts on history and technology on Substack.

Monetizing SaaS:
- Youtube: https://www.youtube.com/@schematichq
- Spotify: https://open.spotify.com/show/5yjegk5duBz3LtvjwOo8ai
- Apple: https://podcasts.apple.com/us/podcast/monetizing-saas/id1757006729

Fynn Glover

the first physical copies of "You're Leaving Money on the Table - How to Create Leverage with Pricing" just arrived. 

first book i've written. really cool to see it in print.

thanks to the many folks who helped bring this together!

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Podcast dedicated to stories from operators about monetization, pricing, and packaging in the world of B2B SaaS

Monetizing SaaS

Co-founder & CEO of Schematic | helping SaaS & AI startups monetize smarter and faster

I'm a co-founder & CEO of Schematic. It's far too complex for startups to monetize features and manage subscriptions. Schematic is the fastest way for the next generation of startup and AI developers to implement and manage pricing. Feature flags, access control, plan & subscription management, metering, and drop-in billing components -- all in one. 

As a kid, I wanted to play professional soccer, and I pursued that into my early 20’s, playing collegiately & then semi-professionally. 

My professional journey off the field began with a community visioning campaign to help continue Chattanooga TN’s revitalization, then a short, but formative stint with an edtech startup, which got me interested in startups, and then a year at a fund of hedge funds, before founding my first company in 2012, RootsRated.

Founding RootsRated kicked off a decade-long journey into building startups. RootsRated began as a go-to site for outdoor recreation and adventure travel. We later pivoted to SaaS, launched Matcha, a content marketing platform, and eventually, were acquired by Springbot, an email marketing service. After Matcha, I joined Automox, a leading ITOps platform, where I wore multiple hats—Director of Growth, Chief of Staff, and VP of Ops. Among other things, I led pricing at Automox, which led to the founding of Schematic. 

I grew up in Chattanooga, spent the last 6 years in Atlanta which is one of the great cities, and recently moved to Colorado with my wife, two kids, and two dogs. Attended the University of Richmond, captained the men’s soccer team, and studied International Relations & French (though my French has since atrophied). 

Outside of work, I enjoy trail running and cycling, and occasionally share my thoughts on history and technology on Substack.

Monetizing SaaS:
- Youtube: https://www.youtube.com/@schematichq
- Spotify: https://open.spotify.com/show/5yjegk5duBz3LtvjwOo8ai
- Apple: https://podcasts.apple.com/us/podcast/monetizing-saas/id1757006729

Youssef Salah

What would happen to your business if you allocated just 10% more of your time to turning pricing & packaging into something your company is exceptional at?

Pricing is 50% of the revenue equation. 

Price x quantity = revenue. 

And yet, most companies spend 95% of their time focused on only the "quantity" side.

We obsess over how many times we can sell the product, while the "Price" half of the equation remains a static intuition.

Pricing is a living, breathing thing, just like your product. 

It's a muscle you have to develop, train, and strengthen continuously to unlock its leverage.

If you’re better at sales, product, or engineering than you are at pricing... ask yourself why.

Pricing is half the battle. 

Make 2026 the year that you treat it like the mission-critical discipline it is.

And leave a lot less money on the table.

Price is a number. Pricing is an architecture.

Most founders blame their billing tool when they can't launch new pricing fast enough.

They're looking at the symptom, not the cause.

The real problem? A broken pricing architecture.

I learned this the hard way at my last company. We had:

Stripe for self-serve

NetSuite for enterprise

Salesforce for our pricebook

Amplitude for usage analytics

Hard-coded entitlements scattered across the code base. 

A homegrown metering system nobody trusted

Six disconnected systems. Thousands of lines of billing code. One tier launch took six months. An add-on initiative was abandoned entirely.

As Jalal Iftikhar from Notion puts it: "The real issue is the inability to slice and dice offerings, test and segment, iterate, and learn. Usage-based billing systems are designed to consume events and inform invoices. They're not designed to enable the commercial tinkering that drives growth."

The architectural imperative is clear.

Your pricing system needs key pillars. 

Unified Product Catalog – One schema for every plan, feature, and price across all systems

Decoupled Entitlements – Business logic separated from product code

Real-Time Metering – Transparent usage tracking that calms CFO anxiety

Company Profiles - Easily manage customer lifecycle across access, usage, upgrades, exceptions, etc. 

GTM Control Plane – Non-engineers can iterate on monetization

The result? Companies like Plotly ship & monetize AI products two quarters faster.

Kurt Smith from Fexa said something I think about all the time: 

"Think about all the creative pricing conversations that have simply stopped happening, because people have accepted that their systems make testing impossible."

In the AI era, pricing agility = revenue agility.

The winners will treat pricing like product. They'll architect for continuous iteration, not annual overhauls.

Your architecture determines your strategy. Invest accordingly.

Great pricing isn’t a number. 

It’s an exchange rate between: 1) what customers get; and 2) what they’re willing to pay. 

The mistake I see most teams make is misunderstanding how their product delivers value worth paying for. 

A good way to figure this out is to splice and dice your product and run two simple matrices with real customers:

1) Usage Value: How often is each capability actually used?

2) Perceived Value in Buying: Which capabilities are must-haves vs nice-to-haves vs irrelevant?

Plot them on a 2x2 and four things emerge immediately:

1. Leaders (high usage, high value): These anchor your paid tiers. Put limits here.

2. Fillers (high usage, low value): Table stakes. Required, but not necessarily monetizable.

3. Detractors (low usage, low value): Noise. Cut them or bury them.

4. Add-ons (low usage, high value): Loved by a subset. Perfect for enterprise or expansion.

This 2x2 is your packaging strategy.

Your leaders drive conversion. 

Your limits & add-ons drive expansion.

Pricing & packaging drives growth when it’s designed to move with customer behavior. 

If you want the template I use for this with customers, comment template, and I'll send over.

Our friends at PricingSaaS tracked 498 companies throughout 2025 and just released their findings. The numbers tell an interesting story:

- Packaging changes up 21% YoY
- Credit-based models up 126% YoY
- AI features shifting from add-ons to core plans

The report includes 50+ real examples with before/after screenshots from companies like Atlassian, Figma, Anthropic, and Canva.

We contributed our perspective alongside some of the most thoughtful thinkers in SaaS monetization.

If you're planning any pricing or packaging changes in 2026, this is worth 15 minutes of your time.

Incredible work from Rob Litterst and John Kotowski!

Link to the report in comments.

a founder i was speaking with today was discussing their pov on craft. 

made me think about examples of craft that have motivated me...

here are a few that i think about pretty regularly:

1. jim harrison's novellas

2. the way beckham can strike a ball

3. jonas vingegaard's mountain climbing technique, strategy, and guts

4. Linear's approach to product development

5. Andrew Johnston's approach to selling by way of listening & inquiring. Also RevenueCat's.  

6. pixar's ability to light up imagination at any age

7. litespeed's titanium bicycles 

8. nate bargatze's humor

9. redbull's content marketing 

10. toyota's delivery of insane consistency & reliability

chatting with a customer in SF yesterday where we were asking them what's the worst part about using schematic. 

one of the best ways ive found to improve. 

then we started talking about what's happening in monetization for both AI startups and enterprises launching AI products.  

this is all changing so quickly, but here's how i'd synthesize what i think it is we're all seeing & feeling in terms of jobs to be done. 

1. launch initial monetization (often credits)

2. stop the bleeding with basic limits

3. there's a transparency arms race to deliver great billing ui and customer portals

4. telemetry, both in terms of costs and churn/expansion signal

5. need to iterate and experiment with pricing models and with packaging more then ever before

if you're building ai and figuring out monetization, how would you edit this?

Super excited about what Vladik Rikhter and Tim Olshansky are building. And for their partnership. We're psyched to support their monetization.

CEO & Co-Founder Fencer | The Security Suite for Startups

🚀 Tim Olshansky and I are thrilled to unveil Fencer - the best security suite for startups (yes, we’re serious, it’s the best!) 

We’ve spent the last 16 months building Fencer with a great team and a couple dozen beta customers. Now we’re opening up to the rest of the world.

At Zenput, enterprise security requirements entered the picture early. When we had fewer than 30 employees, SOC 2 compliance became a prerequisite for revenue growth, and there was no clear, simple solution to help us get there. 

Startups shouldn’t have to juggle 10 different vendors, use non-developer friendly tools, or spend weeks trying to deploy solutions. Security should be simple and accessible for startups, and that is the big idea behind Fencer. 

As one of our customers said: 

“I like to think of Fencer as our co-pilot to help us manage security. Almost like a colleague that nudges us when we're writing code that might not be secure, telling us when an AWS change might have a vulnerability, and monitoring and ensuring that our systems are working in the background as intended and in a secure way.” Prithvi Narasimhan from Rely Health.

Here’s what we’re bringing to the table:

- Unified vulnerability detection and remediation support covering code, attack, surface, cloud infrastructure, and endpoints.
- An integrated SIEM 
- Connections with GRC tools (shoutout to Vanta & Drata) that streamline audit prep

💰 We’ve raised $5.5M from MHS Capital, Goldcrest Capital and a lot of great operators/founders: Shyam R., John Clarke Mills, Satjot "SJ" Sawhney, Harman Singh Narula, Jeff Kahn, Ari Baranian, Alok Chanani, Jackson Noel, Idan Perez 🐙 , David Karel, Nikki Perry, Josh Breinlinger, Robert Sverbilov, Michael Monu, Ash Fontana, Gene Karshenboym, Albert Bielinko, Ben Wheeler, & Gene A. Glekel amongst others.

If you've recently achieved SOC 2, ISO 27001, or HITRUST certification — or already hold one of these — send me a message, reply in the comments, or check out the site:

Open article: Fencer: Integrated Security Platform for Startups by fencer.dev

Fencer: Integrated Security Platform for Startups

Incredibly thoughtful post from my friend Kayvan Dastgheib-Beheshti. thank you sir!

VP GTM Operations @ Payscale | Top RevOps Mentors 2026, 2025, 2024 | Pavilion RevOps Leader of the Year Finalist

View Kayvan Dastgheib-Beheshti’s profile

This might be a surprise, but your product catalog is the forgotten product.

When Fynn Glover asked me about the biggest monetization bottleneck in SaaS, my answer was immediate:

"The product catalog itself."

Here's what is often forgotten entirely - the product catalog and entitlements are as much a product as your actual product. Together, they govern how you monetize. Yet most companies treat them as an afterthought.

I see this pattern everywhere:

Your CRO looks at CPQ as the source of truth. Your CFO looks at the billing system. Your CTO/CPO looks at your database. Your CS leader looks at the admin panel or your CS tool.

Four teams. Four sources of truth. Zero coherence.

The result? Every pricing change becomes a cross-functional nightmare. Engineering files tickets or redeploys. Finance reconciles discrepancies, and points to historical revenue recognition. Sales & RevOps operate with outdated information or rigid legacy structures. Product lacks visibility into the financial impact of their roadmap. It's extremely manual to manage customer lifecycle. 

The structural flaw is simple: businesses under-appreciate that the product catalog needs to be a singular source of truth that orchestrates changes across the entire quote to cash stack. 

As Fynn writes in his new book, You're Leaving Money on the Table, the solution is starting with a unified product catalog that serves as the canonical source for packaging, pricing, provisioning, and analytics. 

One schema. One truth. Everywhere.

When you get the architecture right, speed follows. In 2026, pricing agility IS revenue agility.

Highly recommend that RevOps leaders work cross-functionally to end siloed product catalogs and start treating your product catalog like the revenue-critical infrastructure it is.

Startup Advisor • Growth Leader • Superhuman • Advisor @ Clay, Replit, Wispr Flow, Superpower & others

This is what $1bn looks like.

$1,000 in cash on the table.
$999,999,999,000 in insights from the book.

You're Leaving Money on the Table
How to Create Leverage with Pricing
by Fynn Glover

A field guide to pricing that every founder should read.
Because your startup won't be a unicorn if you get pricing wrong.

If you'd like a copy:

1. Like this post
2. Comment "book" and I'll send it over

4 good times to use WTP & rule of thumb is to hold these conversations on consistent basis to continuously learn. 

1. Pre-product & want to test viability of your solution

2. Working to close design partners/early customers and need to determine price they are willing to pay

3. 6-12 months into a contract with a healthy customer to better understand your value to them

4. Ahead of a meaningful P&P change post PMF

SaaS margins dropped from 90% to 50% with AI.
It’s time to reconsider pricing.
But that's easier said than done.

Most founders panic when it's time to talk pricing with customers.
They overthink it. They undersell.

They lose deals not by asking too much, but by failing to understand what customers actually value.

Fynn Glover has conducted countless willingness-to-pay interviews over the last 2.5 years. He's also trained hundreds of founders on this skill.

His take is simple: willingness-to-pay conversations are critical for finding Product-Market Fit. He calls these talks “pricing therapy.”

Here's his repeatable flow:

1/ 𝐂𝐨𝐧𝐭𝐞𝐱𝐭 & 𝐅𝐫𝐚𝐦𝐢𝐧𝐠
Explain your product's promise. Get the buyer in the right mental model.

2/ 𝐏𝐞𝐫𝐜𝐞𝐢𝐯𝐞𝐝 𝐕𝐚𝐥𝐮𝐞
Ask what problems they think it solves, and which features feel indispensable.

3/ 𝐑𝐞𝐥𝐚𝐭𝐢𝐯𝐞 𝐕𝐚𝐥𝐮𝐞
Compare your value to the tools they already pay for to gauge worth.

4/ 𝐏𝐫𝐢𝐜𝐞 𝐌𝐞𝐭𝐫𝐢𝐜
Explore which metric best maps to their perceived value (seats, usage, etc.).

5/ 𝐏𝐚𝐜𝐤𝐚𝐠𝐢𝐧𝐠 𝐒𝐜𝐡𝐞𝐦𝐚
Show draft tiers and ask what resonates and what feels off.

6/ 𝐌𝐚𝐱𝐢𝐦𝐮𝐦 𝐖𝐓𝐏
Ask for the max they'd pay, either open-ended or scenario-based.

7/ 𝐈𝐧𝐟𝐥𝐮𝐞𝐧𝐜𝐞 𝐃𝐫𝐢𝐯𝐞𝐫𝐬
Uncover the real factors: budget, comparables, frequency, stakeholder buy-in.

8/ 𝐅𝐞𝐞𝐝𝐛𝐚𝐜𝐤 & 𝐄𝐦𝐨𝐭𝐢𝐨𝐧
End by asking how the conversation felt. Listen for discomfort, not just answers.

Make sure your interview is conversational, not static. 

Conducting PMF conversations should never stop.
They should occur when you're pre-product, after you've won initial customers, and on an ongoing basis as you extend and deepen your fit.

Pricing isn't just a number you stick on the product.
It's a conversation about value, confidence, and how well you've done your homework.

🎓 New article packed with actionable pricing frameworks: https://lnkd.in/dW_hDJYi
1. The “wirecutter” guide to modern pricing models with examples
2. How to conduct willingness to pay research - aka “pricing therapy” interview with 8 questions to ask
3. Anatomy of a great pricing page

How do you talk pricing with your customers?

Built a Claude skill for launching credit-based pricing.

After helping dozens of companies implement credit systems at Schematic, we've seen the same challenges come up repeatedly:

1. Teams underestimate the edge cases (credit expiration, refunds, disputes)

2. Strategic decisions happen in silos (finance doesn't talk to engineering until it's too late)

3. Implementation gets scoped as "just a balance field" when it's actually 6+ systems

So we built a Claude skill that walks technical teams through the entire launch from strategic validation to production implementation.

What it covers: 

→ Strategic validation (is credit-based right for you?) 

→ Core decisions (value metrics, expiration, revenue recognition) 

→ Technical implementation (usage collection → balance management → enforcement) 

→ Edge cases (refunds, upgrades, prorations, disputes) 

→ Build vs buy analysis

Try it yourself:

1. Download the skill from GitHub

2. Upload to Claude (Settings > Skills)

3. Ask: "Help me think through launching credit-based pricing"

I'm definitely looking for feedback: If you're building or have built credit-based pricing, what did we miss? What would make this more useful?

Link to repo in comments

taplio

The Battle

Nathan Parcells

Fynn Glover

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