254 Issues And 18K+ Readers Later: The Enterprise Weekly Newsletter Story
We’re Writing the Next Chapter — Come Join Us!
One of the things we get asked about frequently at Work-Bench is our Enterprise Weekly newsletter — the newsletter we’ve been writing and sending out every Friday for the past 5 years, now with over 18K+ readers.
I would never have guessed that when starting a VC fund how much content marketing is part of the job, but here we are :)
When we started the newsletter in 2014, we wanted to come up with a source of top enterprise news and trends. As a VC fund, we were already reading and tracking these companies as VCs— so we thought: could we put it into a newsletter and share it with our greater enterprise community?
We’re proud that our newsletter has led to a continuous loop of positive inbound around all things enterprise tech and NYC — be it an introduction to a marketing executive who just moved to NYC, an early seed stage enterprise startup for us to track or meet, or just incredibly positive and kind feedback (thank you!).
The practice of consistently publishing our weekly editorial has helped us extend our reach and voice across the country and more importantly we hope, get folks as excited about enterprise tech as we are.
We’ve learned a few lessons over the years in writing this newsletter, that we thought may be helpful to share:
1. Visually, We’ve Remained the Same…
You can see visually our format hasn’t changed and we’ve largely stuck to a clean, streamlined design. Maintaining our minimalist signature black and green palette has allowed us to spend time and attention on what truly matters the most — the content!
2. No, You Unfortunately Can’t Automate It Quite Yet
As much as we (especially as an enterprise VC fund :) would love a world in which AI and machine learning algorithms can write our newsletter…we haven’t found the technology to be quite there yet.
That means every part of our newsletter is hand-written and curated:
- Lede — key headlines and news of the week
- Articles — noteworthy articles and news pieces broadly relevant within enterprise software.
- Upcoming Events — select enterprise events here in NYC
- Company of the Week — we generally highlight an enterprise seed startup that recently raised
- Startup Job of the Week — we added this section to support our startups and other companies in NYC community who are hiring
- Fundings & Exits — we track enterprise fundings across the country. While Crunchbase and Pitchbook shows all new fundings, we curate further within our guidelines/definition of enterprise software, which requires judgement calls
3. It’s a Group Effort with Shared Ownership
Given how much time it takes to write and produce each issue (roughly 5–6 hours in all), we have tested a few different approaches to writing the newsletter as a team.
In our early days, we had a dedicated editor on the communications team to produce the newsletter. We now have a streamlined team-based approach in which everyone on the investment team takes a weekly turn co-writing the lede along with our amazing analyst Priyanka, who also sources the fundings and articles. Addie, from the operations team, highlights all community events and meticulously prepares each draft in Campaign Monitor, our email marketing platform, for delivery. And we can always count on our Kelley Mak to come up with the most punny of Subject lines!
After heavy proofing, the week’s lead will sign off with ‘STS’ (ship that $h*t). There are few things like the adrenaline rush and pressure that comes from pushing the “Send” Button to 18K people every week :)
4. Metrics Tell Only Part of the Story
We’re happy to report that we consistently exceed Campaign Monitor’s average email benchmarks in our weekly editions:
- Industry average open rate: 17.92% — Enterprise Weekly performs at average of 31.5%
- Average click-through rate: 2.69% — Enterprise Weekly performs at average of 14.7%
Yet beyond these numbers, it is also anecdotal wins we have accumulated — be it a CIO of a recently IPO-ed company reaching out to get involved with us on corporate engagement, other investors reaching to connect with one of our new investments, growing our Work-Bench brand coast to coast, and kind feedback like the one below.
One set of metrics we thought would be fun to pull— how many times did the enterprise giants feature in our subject lines? 😂
- Google: 32
- Microsoft: 22
- Amazon / AWS: 18
5. The Next Chapter — Join Us to Help Us Write It!
As with everything we do here at Work-Bench, we constantly push ourselves to be creative, hustle, try new things, and understand how we can better support our startups and greater community.
Writing the Enterprise Weekly newsletter continues to an investment of time and effort, but we are are incredibly honored to slide into thousands of inboxes every Friday afternoon.
After 5 years, we are looking to continue growing this readership community even more — be it webinars based on our investment research, more tactical guides, blog posts, and knowledge share from our 200+ events, dinners, and beyond.
For that, we’re looking for a Head of Content to join our Work-Bench team this fall.
If you are a writer who nerds out on enterprise tech and you have a passion for coming up with ideas, creating net new content, and owning execution end to end, reach out to us at comms@work-bench.com. We’d love to hear a few new ideas around how we can extend our newsletter and greater content platform here at Work-Bench.
And to our readers — as always, if you have any suggestions around what you’d like to see more of in our Enterprise Weekly, we’d love to hear from you at comms@work-bench.com on how we can make our newsletter even more impactful.
Here’s to another 5 years (and more!) of great enterprise news.
