James Raybould

Speak

After 7 years helping lead LinkedIn Learning and 4 years intensively learning Spanish, working at Speak is a great fit. I'm helping Speak reinvent the way we learn anything, starting with languages. I'm helping across product and go-to-market as Speak approaches $50M ARR at growth rates well north of 100% YoY.

Fractional GM Exec

Stealth AI Startup

Partnering with a co-founder/CEO who already co-founded one of the defining AI companies.

Fractional Exec at StealthCo

inVest Ventures

I was one of the co-founders to launch inVest Ventures: our ~$2M VC fund connects LinkedIn alumni founders with LinkedIn employees past and present as not only a source of funding but also a source of advice, relationships, and support. I'm inVested.

Advisor and inVestor

Blueprints

Alongside my longtime LinkedIn colleague, John Mayhall, we geek out about frameworks from our favourite operators: the shortcuts and heuristics they use to turn uncertainty into a clear path forward.  

We publish a new Blueprint every few weeks - there are 20+ as of September 2024 - weaving in our own experiences + some cartoon design fun into each one.

Co-Founder and Co-Creator

Stage 2 Capital

The Stage 2 Capital Catalyst supports early-stage B2B software companies in scaling their businesses by combining Venture Capital and Go-To-Market, empowering founders with hands-on coaching from a network of go-to-market leaders.

Limited Partner, Stage 2 Capital Catalyst

WisdomAI

After spending my Bain and LinkedIn days using data in all manner of ways, I loved partnering with the WisdomAI team to put data insights at the fingertips of every employee. Mainly helped on the GTM front, creating marketing assets across core website, videos, blog posts, analyst decks, PR, and more.

Fractional GTM Exec

Getting Super Fit Again 

After my 30s largely revolved around work and our then infant kiddos, on turning 40, I decided to return to my endurance athletics roots. I strove - and largely succeeded - to get as fit again in my 40s as I was aged 18-25 when my life largely revolved around competing in Stanford Crew and semi-professional triathlon:

MARATHON SWIMMING (July 2022 - Aug. 2023): I spent ~20 hours/week training for a range of marathon cold water swims without a wetsuit:
* San Francisco Bay: Candlestick Park to Ghirardelli Square (10 miles), Golden Gate Bridge to Bay Bridge (6 miles), Around Angel Island (5 miles)
* Other locales: Lake Tahoe Full Width (12 miles), Portland Bridge Swim (11 miles), Croatia Coast (10 miles), Half Marathon in a 25-yard pool (13.1 miles). Started but didn’t complete crossing the English Channel (21 miles); I picked a bad day to have a bad day.
* Watched the entire “The West Wing” (156 episodes) in 40-minute, up-to-the-neck, cold-plunge soaks in 12 degrees C/53 degrees F water to acclimate my body to cold water. Not recommended to anybody.
* Gorged on cheese and ice cream to gain ~15 pounds in the "wrong places" to mimic the blubber found in sea mammals to acclimate to cold water. Also not recommended to anybody.
*[For the nerds] Got resting heart rate to 41. 

HIGH VOLUME PUSH-UPS (Jan. - Aug. 2021): During pre-vaccine COVID, while housebound, I decided to do too many push-ups, highlighted by:
* 1,000 push-ups in <1 hour (5-6 every 20 seconds)
* 3,000 push-ups in <6 hours (8-9 every 60 seconds)
* [For the nerds] For 1,000 in <1 hour: 6 every 20 secs, then 5 every 20 secs 

ROAD BIKE RACING & TOURING (Oct. 2017 - June 2019)
* Raced for SunPower Alto Velo cycling team in ~30 Northern California races, ending abruptly with a nasty crash, broken scapula, and immediate “retirement” (see pic)
* Biked 850 miles from LA to Albuquerque over 7 days
* [For the nerds] Reached Functional Threshold Power (FTP) of 340 Watts (~4.5 watts/kg) + climbed Old La Honda in 17:05

Elite Endurance Athlete

LinkedIn

After 5+ years on the Go-To-Market (GTM) side of LinkedIn, first in sales and then in marketing, I spent 7 years in LinkedIn's product team, building out a complementary R&D and then General Manager skill set.

My first product leadership role was plugging into Lynda.com following LinkedIn's 2015 acquisition, building, launching, and scaling LinkedIn Learning. My team's primary focus was our Enterprise business, where we grew revenues >10X from 2015-22, becoming the market leader in Enterprise learning. 

Starting in mid-2020, I added product responsibility for Glint, a 2018 acquisition in the employee engagement space, and acted as the primary Point of Contact with LinkedIn's executive team after Glint's two co-founders departed. I partnered closely with Microsoft leadership, culminating in Glint fully moving from LinkedIn to join Microsoft in April 2022 as part of its Viva product suite. 

Apr 2021 - Sept 2022: Senior Director of Product. Spanning LinkedIn Learning and Glint, I led a team of 13 PMs, including managing Product Directors and LinkedIn's only Senior Principal Product Manager (SPPM).

Apr 2018 - Mar 2021: Director of Product. Led the Enterprise Growth product team within LinkedIn Learning.

Apr 2017 - Mar 2018: Group Product Manager. I shifted from being an individual contributor Product Manager to managing a team in 2017. 

Oct 2015 - Mar 2017: Senior Product Manager. Following LinkedIn's $1.5B acquisition of Lynda.com, I returned to an individual contributor (IC) role. I led the Enterprise side of our Learning Solutions product team, taking "LinkedIn Learning" from inception to a fully launched product in September 2016.

Senior Director of Product, LinkedIn Learning

I enjoyed partnering with the incredible LinkedIn Learning content team to author a 30-minute "What's the So What?" business writing course, building on some of the ideas I learned at Bain and LinkedIn.

LinkedIn Learning Instructor

After 3.5 years in the Analytics & Insights world, I took the "intelligent risk" to take a role leading marketing for LinkedIn's Talent Solutions (LTS) business, a $1B and then $2B business, ~60% of company revenues. I was drawn to the role to learn how to take over an existing team and to build out my marketing skillset.  I was also excited to continue as a member of the leadership team for LinkedIn's Global Sales Organization (GSO), representing all of marketing. Highlights included:

* Expanded our team to ~100 with very high employee engagement scores and very low attrition 
* Product mktg team won several MVP awards, drove go-to-market for multiple major launches
* Grew mktg sourced bookings by >80%, lifting mktg's share of total new $ from ~25% to ~40%
* Introduced customer lifecyle mktg at meaningful scale via digital, automated nurture programs
* Built LinkedIn's first dedicated pricing function

Team's scope spanned PMM, content & digital channels, demand gen & customer mktg

Senior Director of Marketing, Talent Solutions

Looking to develop my management and leadership abilities by bringing together our research and analytics efforts, I co-founded and led Insights for LinkedIn's Global Sales Organization (GSO), spanning 2K+ employees: our 70+ person team's mission was to create research & data-driven insights to power the world's most effective sales & marketing. Team highlights included:

* Some of highest employee engagement scores across entire Global Sales Organization
* Launched "Merlin," an internal website offering easy access to compelling insights for our sales teams to share with prospects and customers. At year-end, Merlin was chosen as one of LinkedIn's Top 10 most transformative stories of 2011 by our executive team 
* "Magic Wand" to automate creating highly customized PPT presentations for sales & execs
* The InDemand Rankings & Talent Brand Index (TBI) to measure companies' talent brand
* Received the 2011 "Leverage" award (one of 3 top global awards) as voted by ~1K-employee Global Sales Organization (GSO) for the extent of the impact on our field sales businesses

Director of Insights & Business Analytics, Global Sales Organization

I was lucky enough to have a huge life change when a former Bain colleague, Dan Shapero, called me up one day and offered the opportunity to join LinkedIn during a phase of hypergrowth. Wanting to move from consulting others to learning how to do, myself and with teams, I excitedly joined a ~500-employee LinkedIn as part of its Talent Solutions business on a combination of business analytics & strategy:
* Partnered with analytics & sales operations to create and operationalize our “Size of Prize” methodology, which meaningfully changed our global approach to account allocation & prioritization 
* Co-developed a series of methodologies and tools to help our sales teams grow our business, including “Bullseye" & "Futurama" for account and lead targeting
* Individually received the 2010 "Leverage" award (one of 3 top global awards) as voted by the global Talent solutions team for the extent of the impact on our business

Strategic Solutions Manager

Bain & Company

I returned to Bain San Francisco after HBS for ~18 months:
* Worked with UC Davis's "Wine School" on its growth plan
* Advised leading private equity firm on ~20 investment opportunities  
* Led Bain's Stanford 2009-10 undergrad recruiting to record # of applicants & accepted job offers
* Received all performance ratings in the top "bucket"

Consultant

The Bridgespan Group

During my business school summer, I consulted on strategy for non-profits, specifically the nation's largest provider of mixed-income housing + the nation's largest state-based educational organization

I'm currently enjoying being a fractional exec at two AI startups - Speak and a Stealth Company - while still having time to work on inVest Ventures, a Community VC fund connecting LinkedIn alumni founders with LinkedIn employees past and present, and to partner with my longtime colleague John Mayhall on Blueprints - Frameworks from our Favourite Operators at https://blueprints.guide/

Overall, I'm a Generalist. After Consulting at Bain before and after HBS, I joined LinkedIn in early 2010 and spent 12.5 years moving across functions and leadership roles: I started in Sales Strategy and Analytics before moving to Marketing, then to Product Management, and finally to General Management. 

To tell my longer story, 3 dates from 3 decades help:

Sept. 22, 1995: I travelled 5,000 miles from my London hometown to Stanford. I was drawn to studies, sports, sunshine, and a Bay Area culture more focused on creating the future than curating the past. I rowed on the Stanford Varsity Crew team and studied psychology for my B.A. and M.A. And I've stayed close: I can see the Stanford campus from our backyard.

Sept. 13, 2004: I joined Bain Bay Area as an entry-level Consultant. After a few years of racing triathlon and working in sports business, I was drawn to Bain’s entrepreneurial culture and fast-paced learning environment. Looking back, my strategy and comms chops were forged at Bain, as was a lifelong love of Excel, PowerPoint, and Cinnabon.  

March 8, 2010: I left Bain to join a pre-IPO LinkedIn with ~500 employees and ~$100M in revenue. I was initially drawn to the hypergrowth environment but quickly learned I’d found far more. First, a vision that deeply resonated - to create economic opportunity for every member of the global workforce - and, second, a set of inspiring leaders teaching me how a culture and values focus could underpin incredible businesses. Over the next 12.5 years, my roles and responsibilities varied: in function from sales strategy, analytics & insights to marketing to product to GMing; in scope from being an IC to leading ~100 person teams; and in scale from helping run our largest, multi-billion dollar recruiting business to jumping in to help lead our acquisitions of Lynda.com (2015) and Glint (2018). 

Outside of work, I'm a long-term elite endurance athlete (rowing > Ironman > marathons > bike racing > marathon swimming) and compulsive reader and film-goer. Here's ALL my books & films (bit.ly/z2D1sX) and I publish a "What's the So What?" newsletter distilling favourite books and experiences into what matters most (bit.ly/3q188jL)

Founding Member & Advisor

I’m excited to be a founding member of Round, a newly launched community for tech’s most thoughtful leaders. Since joining I've benefited in a major way from small "core group" meetings, special events with luminaries, connections with other tech leaders, and more. Starting in early 2023 I've also begun to help the Round leadership with a range of projects to help them grow their impact.

Our 8- and 11-year-old kiddos were extra gleeful to insist upon a "6/7" Christmas tree this year 🎄

Putting on my analyst hat: I predict 6/7 trees MASSIVELY outperform this 2025 holiday season

Putting on my business hat: what a missed opportunity for a special promo price and/or photo opportunity to delight the kids

For those not fluent in Gen Alpha: "6-7” is current slang for all manner of things. Perplexity primer for the curious: https://lnkd.in/dfKVYvBD

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100% of you chat with AI assistants daily. But I'd guess fewer than 10% of you have tried building something with AI - because "building" sounds technical and hard. But they're exactly the same skill. 

I'm not deeply technical, but my nights and weekends are now consumed with building: a workout tracker and film site for me, an AI tutor and License Plate Game for the kids. A long backlog ahead that I can’t wait to dig into. 

And although code is being written, I'm not coding - I'm giving instructions. To Replit, Claude Code (from Anthropic), Cursor and occasionally others. I'll learn some Python soon, but from curiosity, not necessity. 

It's the most fun creatively I've had in a long time. Spotify, Wispr Flow for voice input, and building = a flow state that reminds me of long Excel sessions back in the day (without the Bain & Company deadlines). 

If you haven't started because it sounds hard: it's not. Thanksgiving in the US is a great excuse to dive in. My recommended starting point: Replit - it handles everything from build to host. 

And if you're hesitant and want a helping hand, DM me. Happy to try to help you get rolling.

PS: A shout out to Daniel Roth, my old colleague and LinkedIn’s Editor-In-Chief, for the inspiration with his Forward Deployed Editor series -  https://lnkd.in/dzMDP396 - and to another former colleague, Sachin Rekhi, builder extraordinaire, who shared his take on the best AI product building tools - https://lnkd.in/dZW8BSdy

A quick love letter to Superhuman Mail and Notion for making a 6-hour flight (hello, New York!) so much more enjoyable

I'm struck by the polish and delight in both products: both convey that the PMs, designers, and engineers have taken the time to deeply know their user and agonize over every single flow and minor detail. I worked offline - a much tougher bar - and both executed flawlessly

I’ve been a longterm fan boy of Notion - I have 20K+ notes and rely upon it as my digital control centre - but I spent an hour catching up on personal email using the Superhuman Mail iOS app and came away equally impressed: it blends feeling incredibly simple and incredibly powerful, an unusual balance to strike

There’s a famous Steve Jobs craftsmanship story about how his father,  a carpenter, insisted on the backs and insides of his cabinets being made up of high quality wood even though nobody would ever see them. I get this same vibe from the product and UX teams at Superhuman Mail and Notion: they've thought through ALL the corner cases, even the ones that are very very unlikely for most people to ever experience

It’s not a coincidence that co-founders Rahul Vohra (Superhuman) and Akshay Kothari (Notion) also co-founded previous companies that were acquired by LinkedIn: LinkedIn has always had a product-led culture and a great eye for product talent when acquiring companies 

Rahul and Akshay: kudos and thank you for building such amazing products and companies. I can’t wait to see what you’re working on next - my flight back to SF is Friday if you've got anything special shipping before then ;)

I love Wispr Flow even more: below is from Nilesh Kothari, the father of Tanay Kothari (Wispr Flow's co-founder/CEO)

- Peter Yang's takeaways from their podcast (the original post): https://lnkd.in/dZvQ84c2
- The full Podcast episode with Peter Yang & Tanay Kothari: https://lnkd.in/dwX9sbVz

If you're not using Wispr Flow, I promise you you're operating with your "arm" tied behind your back

PS: Akshay Kothari, Notion holds a permanent, special place in my heart, of course, but it's nice to see a different Kothari creating such an incredible product ;)

My AI stack closing out 2025: 12 months ago, half didn’t exist; the rest were shells of what they offer today:

1. BROWSER, SEARCH, & NEWS: Comet from Perplexity and Perplexity in general; my go-to for quick answers on everything

2. EMAIL: Superhuman Mail; once I took the time to customize it and learn the shortcuts, I do indeed feel superhuman

3. MEETING SUMMARIES: Granola; its core product always works, and they’re innovating fast

4. VOICE TO TEXT: Wispr Flow; the biggest habit change I made in 2025 — >70% of my 'typing' is no longer typing

5. VOICE ASSISTANT: ChatGPT Advanced Voice Mode from OpenAI; while driving or walking, I’m probably 50% podcasts, 50% talking to ChatGPT

6. WRITING: Claude from Anthropic and Notion; Claude just gets me, and the Notion integration is incredible, I love the combo

7. BASIC IMAGES: Claude or Claude Code; capabilities here are improving quickly, including creating the image below

8. FANCIER IMAGES: ChatGPT or Gemini Nano Banana Pro from Google; I especially love the new GPT Image 1.5, live as of yesterday!

9. DEEP REASONING: I have the weakest opinion here - I rotate between Claude, ChatGPT, and Gemini, often using all of them for a query

10. BUILDING QUICK PROTOTYPES: Replit; I started with Replit, and its all-in-one nature has never let me down

11. BUILDING MORE POWERFUL SITES/PRODUCTS: Claude Code and Cursor; both turn this non-coder into a (super happy) one-person dev team

12. AUTOMATING FLOWS/AGENTS: Claude Code connected to APIs (e.g., Spotify, YouTube, Notion, news feeds) or using Relay.app; Claude Code is so powerful, Relay.app is a seamless, one-stop shop

🎁 The surprise: no AI products from Microsoft, Apple, or Meta in my daily stack. Only sporadic use of Alexa+ (95% for music/Audible) from Amazon and NotebookLM from Google - until Nano Banana Pro/Gemini 3 last month. 

My daily stack runs almost entirely on companies most of us hadn't heard of before ChatGPT launched 3 years ago. 

And it relies most heavily on Claude from Anthropic, my MVP for personal use cases for the third year running 🏆

If you could recommend one AI product that I’m not already using, what would it be?

Can't wait to see where AI takes all of us in 2026! 🚀

Claude Code is my new favourite Swiss Army Knife for building and creating.

And I write this as somebody who doesn't code.

With Spotify Wrapped dropping this week, I'd normally just scroll through, share with a few friends, and move on. But in today's AI world, I thought: Why not dig into my last decade of Spotify Wrapped data?

A year ago, I wouldn't have done this. It would have been days of digging into spreadsheets, pivot tables, and VLOOKUPs. And then doing my best to fumble with design software to create an infographic.

Using my trusted partner, Claude Code, we built this infographic in under 2 hours:
1️⃣ I had it pull my top 100 songs from each year via the Spotify API
2️⃣ We ran some analysis to find patterns
3️⃣ We iterated on content and design to create the whole infographic.

Claude Code was the ONLY TOOL I used.

No spreadsheets. No Canva or Figma. No copying and pasting between apps.

Claude Code isn't just a coding tool. It's a research assistant, data analyst, image generator, and overall builder all rolled into one. The "Code" in the name undersells it: I'd think of it as Claude Agent or Claude Everything.

On the actual music front, a few fun facts: 
→ Taylor Swift accounts for >15% of my top 1000 songs from the decade: 153 distinct songs! #ProudSwiftie
→ Some songs hit hard for one year, then vanished: "drivers license" from Olivia Rodrigo was my #1 in 2021 and "everything i wanted" from Billie Eilish was my #3 in 2023, neither to be heard again in future years #OneYearWonders
→ The "Frozen" soundtrack and "Truck Tunes" crushed it for a few years when the kiddos were tiny #IMissToddlerDadLife

DM me if you'd like more details about how I did this. I'm not very technical, so Claude Code guided me through the Spotify APIs, and then it was just back-and-forth prompting, super simple.

If you haven't embraced Claude Code yet, you're leaving creative firepower on the table. It's INCREDIBLE.

#ClaudeCodeFTW #SpotifyWrapped #ProudSwiftie

James's Decade of Spotify Wrapped

Claude Code + YouTube API = your own personal video playlist curator

YouTube's algorithm is good, but it's partially driven by ad revenue and what it thinks will keep me on site. I spent <1 hour last night with Claude Code to automate the perfect playlist for me:

1️⃣ Every morning, I'll wake up to 25 fresh videos tailored to my interests:
- 15 videos from my favourite channels (e.g., No Priors with Sarah Guo or 20VC with Harry Stebbings)
- 10 videos on topics I'm interested in (right now, mainly AI and tennis)
- Smart duration filtering: no videos under 60 seconds, at least 5 medium-length (10-19 min), at least 5 deep dives (20+ min)
- Zero duplicates, zero content I've already watched

2️⃣ RUNS AUTOMATICALLY IN THE CLOUD: Using GitHub Actions, this now updates every morning - no computer or prompting needed, completely hands-free and automated

3️⃣ MORE FOCUS, LESS DOOM SCROLLING: Until last night, I'd hit YouTube and get sucked into content I hadn't planned to watch. Now, in theory at least, I'll go straight to my "Latest & Greatest" playlist and stay more on point.

Looking forward, now that I've connected Anthropic's Claude Code, YouTube, and GitHub, I'm excited to build more custom playlists + better understand how much I'm actually watching and on what topics - maybe it'll be all Rafael Nadal highlights and no AI?? ;)

HOW TO DO THIS:
1. Install Claude Code (works best locally; plenty of YouTube tutorials to help)
2. Ask Claude Code to walk you through setting up Google Cloud Console, enabling YouTube Data API v3, and creating OAuth credentials 
3. Describe what content you want in plain English 
4. Connect to GitHub - Claude Code will guide you - to automate the flow daily/weekly

My Claude Code fun with YouTube last night and Spotify last weekend highlights the power of AI to help us personalize our experiences and reclaim our attention. BigTech's algorithms are great, but why not tailor our content to exactly what we want?

Finally, I'd LOVE it if we could more precisely tailor our LinkedIn feeds versus needing to mute people and tune our notifications one connection at a time. I may know enough about LinkedIn - including its API policies and ad business - to know that'll never happen, but a boy can always dream ;)

Excited for more exploration with Claude Code this weekend!

Can't wait to showcase 6 AI workflows for PMs and PMMs this Thursday - please join us!

This Thursday at 12 pm PT, François Dufour and I are hosting a PM/PMM AI workflow fest, with 6 presenters demoing for 6 minutes each:

1️⃣ A Sales Intelligence Agent
​2️⃣ An AI Email Marketer Agent (incl. pulling recent product release updates)
3️⃣ Workflow to go ​from Sales Calls to Insights by Segment
​4️⃣ A Customer Testimonial Video Creator
​5️⃣ A Social-Listener for Growth and PMM
6️⃣ A content curation tool using Claude Code for YouTube & Spotify

Seats are limited (capped at 50), so please request access via the link in  the comments or DM me directly

Will definitely be fun to see what folks have built, including Jacob Bank, the co-founder and CEO of my favourite AI agent automation platform, Relay.app 

PS: OpenAI's ChatGPT rolled out enhanced image generation capabilities today, and they're pretty incredible: so much easier to tune!

Claude Code + Spotify API = music superpowers for all of us

Spotify Wrapped is fun - but it's once a year. I've been using Claude Code to go well beyond what Spotify can natively offer:

1️⃣ CUSTOM DISCOVER WEEKLY FOR PODCASTS: Twice a week, I get 25 podcast recommendations blending new episodes from must-listen shows I already follow - e.g., No Priors from Sarah Guo or The Rewatchables with Bill Simmons - and guests I want to track. E.g., if Andrej Karpathy is interviewed on any podcast, I find out. Think Google Alerts for podcasts, the 2025 AI-powered version, with a completely customized prompt just for my interests

2️⃣ DYNAMIC PLAYLISTS: My "Top 25 from the Last 30 Days" and "Top 50 - All Time" that auto-update based on my actual listening data.

3️⃣ MY DECADE IN REVIEW: Using only Claude Code and the Spotify API, I pulled together a fun look back on a decade of listening on Spotify. Turns out it was >15% Taylor Swift. No regrets :) See here for the 8-page infographic: https://lnkd.in/dN9Xdzmz

WHAT'S NEXT:

1. "AM I BRANCHING OUT?" ANALYSIS: A weekly report to show me how much of my listening is new - songs and artists - versus repeat listening. There's nothing wrong with repeat listening, but I want >30% to be net-new, so I'll get 100 new songs every Monday. Think Discover Weekly, but larger and even more tailored to me.

2. DEEP CUTS I'VE MISSED: An automatically-generated playlist pulling songs I've never heard from artists I already love.

3. FORGOTTEN FAVORITES: Songs I used to play on repeat but haven't touched in 6+ months, automatically brought back into rotation. The musical equivalent of finding a favorite shirt in the back of your closet.

HOW TO DO THIS:
1. Install Claude Code on your computer (you can do this on the web too, but it works best on your machine; any YouTube tutorial will guide you)
2. Go to https://lnkd.in/d4DfER6t
3. Create a free developer app (takes 2 minutes)
4. Get your Client ID and Client Secret
5. Describe what you want in plain English to Claude Code - giving it your Spotify credentials - going back-and-forth until it's exactly what you want

Claude Code handles the OAuth flow, API calls, error handling, scheduling—pretty much everything that sounds complicated and technical, but isn't now that you're using natural language.

MY OVERALL TAKEAWAYS:
1️⃣ Claude Code is amazing - it's fast becoming the single product I recommend most to anybody, even more so if you're not technical
2️⃣ AI assistants let us build in minutes what we'd never have tackled before - the time investment pre-AI was just too prohibitive

What other APIs/integrations are people getting the most out of with Claude Code? I'm all ears and promise not to skip them ;)

My top 10 books of 2025: an unusual year - 8 out of 10 fiction and only 2 published this year:

🥇 James (2024) by Percival Everett https://lnkd.in/d3YM64DZ 
Huckleberry Finn from the perspective of a highly literate and opinionated Jim; IMHO, meaningfully better than Twain's classic (which I reread in 2025)

🥈 Small Things Like These (2021) by Claire Keegan https://lnkd.in/d-ku6ZaS
Brief and unflinching - religious abuses in 1980s Ireland - yet hope and resilience shine through

🥉 Demon Copperhead (2022) by Barbara Kingsolver https://lnkd.in/d7XwDJMW
Longer and just as dark as #2 - David Copperfield retold in present-day Appalachia and the opioid crisis - but surprisingly uplifting

4️⃣ The Running Ground (2025) by Nicholas Thompson https://lnkd.in/dM8xE9EC
My favourite tech follow on LinkedIn penned a beautiful meditation on running and what it means to be both father and son

5️⃣ Train Dreams (2011) by Denis Johnson https://lnkd.in/dkuVvnpF
A quiet, stoic life in the early 20th century, set against the relentless backdrop of change

6️⃣ Olive Kitteridge (2008) by Elizabeth Strout https://lnkd.in/d_a-6xY2
Rare to enjoy a protagonist who's so infuriating and endearing in equal measure, all set in lovely coastal Maine

7️⃣ Crossing to Safety (1987) by Wallace Stegner https://lnkd.in/djKb74RD
Two couples, decades of friendship, and the slow accumulation of perspective that comes with time

8️⃣ Buckeye (2025) by Patrick Ryan https://lnkd.in/dYPBCquE
Shares DNA with Crossing to Safety: family bonds, the weight of ageing, and adapting to change

9️⃣ Playing to Win (2013) by AG Lafley & Roger Martin https://lnkd.in/dKqN75Tu 
A clear, easy-to-act-on, timeless framework for corporate strategy, made concrete through real examples

🔟 The Lincoln Highway (2021) by Amor Towles https://lnkd.in/d-p54V_E
Not as good as A Gentleman in Moscow, but compelling characters and page-turning prose carry you along

Overall, I read mainly fiction this year - including several books set pre-1975 - to take a break from work and the (amazing) AI future rapidly approaching. I consume so much bite-sized tech content via LinkedIn/X, LLMs, podcasts, etc., that extended periods of time to read longform fiction are therapeutic

With the holiday reading season here, what did you love this year?

PS: Claude Opus 4.5 built the image, and Claude Code & Cursor helped me build a site capturing the 700+ books I’ve read: https://lnkd.in/dcvW6rks

Learn and showcase the best AI workflows by PMs and PMMs - and you might win not only bragging rights forever, but a year of Augment Code 🏆

My marketing guru friend François Dufour and I are hosting an invite-only AI Workflow Fest next Thursday, Dec 18, at noon PT, featuring the PMs and PMMs who've gone well beyond the basics with AI. Not technically a PM or PMM? Submit and join anyway.

👉 Link in comments to submit your favourite workflows. Submit by this Saturday, Dec 13. We'll select ~6 of the most original to present live. 

We want to see the agents and workflows you've built and rely on - the ones that make you faster, sharper, and more creative.

Top 3 win Augment Code for a year + a LinkedIn post written by yours truly gushing about your amazing creations :)

Everyone who attends will have a good time, we promise. And will get the recording and walk away with ideas to implement immediately.

We can't wait to learn about and showcase what you've built!

👇 for the form to submit

Wispr Flow is in my pantheon of favourite AI products (with Granola, Perplexity, Anthropic’s Claude and Claude Code): I'm dictating this while sitting next to my daughter at a dentist appointment, literally whispering into the phone 

If you haven't tried Wispr Flow yet, I promise you'll love it, especially if you give it a week to change your habits from defaulting to type to defaulting to voice (by the way, Wispr Flow one-shotted this note: Zero edits, all voice)

CEO at Wispr Flow | IOI Medalist | Forbes 30 under 30 | Stanford CS + AI

We just raised another $25M after 10x'ing our ARR in 5 months. The crazy part is this almost never happened.

17 years ago, I watched Iron Man as a 10-year-old kid in Delhi. That night, I pulled my first all-nighter teaching myself to code. Not because I wanted to build apps or make money.

Because I wanted to build Jarvis.

My parents gave me 1 hour of screen time per day. So I coded in secret, sleeping every alternate night through middle school and high school. Built 50+ apps. Got a cease and desist from Google at age 12.

All for this one obsession: making computers understand us like humans do.

Fast forward to today:
- We've raised $81M total to build the voice operating system
- Growing revenue 40% month-over-month this year
- 70% user retention after one year (unheard of in consumer)
- Teams at 270 of the Fortune 500 use Wispr Flow daily

Our Series A2 was led by Hans Tung at Notable Capital (who was an early investor in five companies that made it to $100B valuation like Slack, Tiktok, and Airbnb). Steven Bartlett also joined as an investor and partner. 

But here's what matters more than the money:

We cracked voice input. Not transcription - actual understanding. Our users hit "send" in under 0.5 seconds without checking. They trust it blindly. That's never existed before.

In a recent benchmark, Wispr came out as 3-4x more accurate than OpenAI, ElevenLabs, and Siri. 

And we're just getting started. Voice input was step one. Now we're building the assistant that actually does things for you.

To my co-founder Sahaj Garg - there's no one else I'd rather build Jarvis with than my college roommate and closest friend.

To our team pulling all-nighters and shipping magic - you're the reason that 10-year-old kid's dream is becoming real.

We're hiring cracked engineers and growth marketers who want to build the future of human-computer interaction.

The keyboard had a good 150-year run.

Time to build what comes next.

PS: like, repost, and comment "Wispr" to get Wispr Flow for free for 3 months ❤️

— Written with Wispr Flow

As usual, Reid Hoffman outlines where the future is going better than the rest of is. Wispr Flow and using voice versus keyboards is exactly where it's going and it's so exciting and is already here

Open article: What if we got rid of the keyboard?  by Reid Hoffman • 2 min read

After 10+ years of Amazon Echos in our house, Alexa+ finally feels like AI

Is it as conversational as OpenAI's advanced voice mode? Nope. 

Does the underlying AI feel as powerful? Nope. 

But just saying "Alexa" or "Ziggy" (my personal favourite) means zero friction. No unlocking. No typing. No tapping. Just talking.

Overall, it just makes me more excited about where wearables take us next, whether a Pin or Glasses or something else, so that our AI assistants are always available to us in a "no touch" manner.

BTW, if Google or Apple have something better, I'm all ears. Especially if there are Cyber Monday sales ;)

Timeless Leader

My life's work is to support you - an everyday leader - on your journey to build a positive, lasting legacy... when you barely have time to get through your daily to-do list.

There are two key pillars to Timeless Leader. 

The first is broad-based research, advocacy, and education about how a group of people can sustain leadership in pursuit of ambitious goals. It's not about what the person at the top of a giant org does, but about how leaders of small orgs and communities share and exchange power over time to deliver change. 

This is where you start. Subscribe to my newsletter and engage with me here on LinkedIn. It's free, and we're just getting started. 

The second pillar is closer partnership with leaders of small organizations who lack full executive leadership teams and support staff. Usually 10-50 person companies lack staff in crucial functions like HR and marketing, and might have a COO, EA, or Chief of Staff - but rarely all three. 

In these situations I run time-bound projects to set vision, develop actionable strategies, and support strategic execution. We call this work "Fractional Chief of Staff" services and the difference it makes is profound: 

- Remove ambiguity and inertia in the organization and enhance CEO leadership skills
- Save 20+ hours on research for key solutions like GTM or HR tech and agencies
- Make better decisions on external partners, ramp them up, and get results
- Save up to 70% of personnel costs as you stand up new functional orgs

Need a partner to shorten your transformation or growth timeline by 12-24 months? Book a call in my featured section.

Founder, CEO, and Principal Consultant

Edstruments

Fractional Chief of Staff, supporting partnerships, marketing / lead gen, talent development, and strategic planning.

Chief of Staff

Slate

Led marketing, partnerships, and GTM operations. 
➡️ Represented Slate at industry trade-shows (Transform, HRMI) and led event strategy. 
➡️ Refined outbound GTM motion to focus on target accounts and high intent personas.
➡️ Led partnerships with major HRTech vendors, including co-marketing, co-sell, and referrals.
➡️ Initiated CRM migration from Zoho -> HubSpot.
➡️ Led procurement and onboarding efforts for new marketing agency services.

Head of Growth

I led functions, programs, and projects that supported the doubling of Box's revenue at scale (to $1B), while achieving GAAP profitability, and preserving and evolving an award winning culture. Across each of these roles, I aligned cross-functional stakeholders and global teams to a common vision and enabled them to execute in the service of business growth and transformation, often in the face of intense macro pressures. 

🚀 As Senior Manager of Employee Growth and Experience (2021-2023) I led and executed global leadership development and manager enablement for 500+ stakeholders. 
🚀As Senior Manager of Growth and Strategy (2019-2021) I led and executed the strategy and program management function for the global professional services organization (100+ team members, $XXM revenue)
🚀As Manager of Marketing & Customer Success Strategy (2017-2019) I led strategic projects to launch a new product (Relay), a new team (Technical Account Management), and a new operating model (customer engagement).

Efficient Growth & Transformation

Apostrophe 3

Supported board governance, growth strategy, core operations, and business development. Through creative media and corporate partnerships helped sell over $100M of luxury real estate in the NYC area.

Board Member

Democracy Prep Public Schools

I played a key role in expanding Democracy Prep from one to six high schools.

Curriculum & Assessment; Scaling Organizations

Council on Foreign Relations

I developed strategic plans and key assets for Model Diplomacy, an online learning simulation (part of CFR's Global Literacy Initiative).

Learning and Development Consultant

Civic Games

I recruited cofounders, built the team, set the vision, and drove execution across all functions. In two years we built three products and several service offerings that we sold into schools across the country. With a small addressable market we struggled to fundraise, and with limited capital struggled to realize the product vision. After 2+ years full-time, my co-founders and I decided to dissolve the venture to pursue other opportunities.

Co-Founder & CEO

BRONX PREPARATORY CHARTER SCHOOL

I taught 10th and 11th grade world history and led students to significant gains in writing & year-over-year improvements on Regents scores. I launched an initiative to take students on trips aboard, and led a trip of twenty-two students and nine faculty to seven cities in Spain.

World History Teacher

NYC Department of Education

"Selected from approximately 20,000 applicants nationwide to join national teacher corps of recent college graduates who commit two years to teach in under-resourced public schools. ." --From TFA

I taught 9th grade global history at the New Explorer's High School in the Bronx. I served as a founding member of the data inquiry team and pioneered the use of data in the classroom.

World History Teacher, Teach for America Corp Member

Strategic Chief of Staff, Operator, & CEO Partner | Leadership Expert | Writer & Community Builder

As someone who taught world history before entering business, I'm drawn to the patterns that separate lasting legacy from temporary success. I now partner with time-starved executives to transform urgent pressures into essential outcomes through my "Timeless Leadership" approach. 

MY METHODOLOGY:
→ SAVE TIME (Leading Self): Curating commitments at a micro and macro level 
→ MAKE TIME (Leading Orgs): Translating values & insights into velocity & impact
→ ESCAPE TIME (Leading Movements): Scale and sustainability through teaching & partnerships

RECENT RESULTS:
→ Fractional Chief of Staff at Edstruments: Established 3 new partnerships, AI-enabled GTM motions, and scalable OKR, employee engagement, & talent development programs
→ CEO Training Program: Established digital training program for 30+ executives at Alpine Software Group, spanning core strategy, product, and GTM best practices
→ Box Scaling Success: Led strategic program management across marketing, customer success, and HR orgs, enabling growth from $492M to $1B

Whether it's sprint planning or succession planning, quarterly OKRs or 10-year vision—I help leaders operate effectively at every timescale while building sustainable competitive advantage.

CORE SKILLS AND EXPERTISE:
- Strategic Partnership & C-Level Advisory
- Startup & High-Growth Company Operations
- Organizational Transformation & Change Management  
- Project Management & Cross-Functional Leadership
- Education Technology & SaaS Domain Expertise
- Data-Driven Decision Making & AI Integration

Currently I provide fractional Chief of Staff services to mission-driven organizations, write a weekly Substack newsletter for everyday changemakers, and lead a monthly community gathering for committed Timeless Leaders. 

I am open to FT Chief of Staff roles with companies intentional about their long-term impact. 

Need a hand to build something that matters? Let's connect.

taplio

The Battle

James Raybould

⏳Joe Ballou⌛

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taplio

The Battle

James Raybould

⏳Joe Ballou⌛

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}James Raybould's LinkedIn Performance

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