What's 🔥 in Enterprise IT/VC #182

Q2 enterprise sales at a 🐌 pace

As we’re done month 1 of Q2, it’s pretty clear that it’s going to be a rough quarter for most companies. While sales activity seems to be increasing across the board in webinar traffic and visits to websites, activity does not equal 💰 and closed sales. Many large companies continue to come back to startups to negotiate payment terms and get out of contracts early. This famous Far Side cartoon pretty much sums up what most in enterprise sales are experiencing save for the companies who are getting a Pandemic boost. For example, SAP, amongst others, recently warned that “a significant amount of new business was postponed” toward the end of the period.

Interestingly enough, many of those enterprise startups who are getting a “boost” during this pandemic were already strong to begin with. Companies like Confluent (raised $250mm at a $4.5 billion valuation), Airtable (in talks now to raise $50mm at $2.5 - 4 billion price), and Blue Prism (raised $125 million at a $1.25 billion valuation). These companies were also in strong categories as cloud, automation, and collaboration are still must-haves for many enterprises.

Similarly those Fortune 500s who invested heavily in their digital presence pre-COVID are getting rewarded during this crisis. Target is a prime example as their Q1 numbers show what software and a team of 3200 software developers can do to revenue.

All Fortune 500s will continue to speed up their move to the cloud and developer software, devops and anything cloud related will continue to be one of the bright spots in enterprise software.

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Scaling Startups

  1. Must listen! Rahul Vohra (Superhuman, a portfolio co) is back for an encore on the Twenty Minute VC, one of my favorite podcasts. Rahul shares how he scaled from bespoke 90 minute onboardings to hiring his first onboarding specialists and the math behind scaling to $100 million ARR. He also discusses how game design influences much of the product in Superhuman.

  2. Thought provoking piece from John Luttig at Founders Fund. Well laid out argument worth reading, and while I don’t agree with all, lots of interesting nuggets for founders. Net net he argues for VCs investing more in R&D - not sure how new that is as that is what we do at boldstart, investing in visions, but what does speak to me is several areas are maturing and very little “new” ideas so startups need to arm themselves to compete with each other.

  3. Jeff Lawson from Twilio shares his COVID playbook - founders I highly encourage you to click through for the tweetstorm - employees, customers, and use balance sheet to emerge stronger.

  4. Bill Gates writes a piece in the Economist on how to fight future pandemics and shares when he thinks a vaccine will be ready. IMHO, until then, it will be stop and go for awhile so start thinking second half 2021 when we may return to some sense of normalcy.

    My hope is that, by the second half of 2021, facilities around the world will be manufacturing a vaccine. If that’s the case, it will be a history-making achievement: the fastest humankind has ever gone from recognising a new disease to immunising against it.

  5. If your startup runs on AWS, here’s a best practices list from Troy Fine to prepare for your SOC 2 Audit.

Enterprise Tech

  1. 🔥up for launch of Env0, a portfolio company. This continues our investment thesis around devops and abstraction of infrastructure so devs can do more faster while orgs have centralized governance. The obligatory “why we invested” post is here. Try it out - Env0.

  2. If your wondering what Okta is thinking about in the future, Todd McKinnon, co-founder and CEO shares some insight - looks like privacy 😃 - Inpher, Prifender, Dataguise.

  3. Bessemer State of the Cloud report is out - lots of great market maps on privacy, remote work, and API first businesses. Also has one my favorite charts which is all about how much faster these companies are scaling.

    FWIW, at boldstart, if you’re already on a VC market map it’s too late for us to invest.

  4. Aaron Levie continues tweeting about digital transformation and spells out the “new normal” for Fortune 500s

  5. AWS getting into automation, starting back-end event driven first and claims not going after Microsoft Power Automate. AWS App Flow is like a high powered Zapier, IFTTT killer - pretty slick way with no code to easily move data from SaaS apps like Salesforce, Marketo, Slack, Servicenow, etc. on scheduled, on-demand or event based. Makes it super easy to analyze a wider variety of SaaS data in AWS but of course, creates more lock-in.

  6. Random…Is this the future of live entertainment, esp. during a Pandemic? 12.3 concurrent players showed up in the Fortnite virtual world to participate, just a matter of time before some of these hybrid consumer/enterprise collaboration apps start marketing in this community.


  1. Shopify CTO says traffic is like Black Friday every day

  2. Discover CEO shares Q1 numbers and the alarming drop YTD in spend in April. Notice the alarming drop and change in most categories in April as most of the US was on full lockdown.