Reflecting on the Productivity Category

My most recent post on LinkedIn cross-posted here.


Having spent the last 4 years working in the productivity category, I wanted to share some learnings from the space. Note, everything below is slanted towards an early-stage startup ultimately selling prosumer to SMB.

1/ Individually vs Group Useful
Sometimes called single-player vs multi-player mode but the premise is the same. Is your app useful to the individual or useful to a group (eg workplace).

For example, Asana is useful in a group but not so much as an individual. Evernote is useful to the individual but not so much in a group. Rare apps like Dropbox are both but this is not a requirement. Given that productivity apps typically touch personal data, they are not generally viral. Brainstorm ways to be both individually and group useful.

2/ Direct-to-Prosumer vs Top-Down
Is your app B2C or B2B – the trend is to drive prosumer adoption and then to sell to the SMB. Yammer pioneered this model; Xobni extended this model and in some instances it can even backfire such as when Microsoft asked their employees to uninstall the Xobni plugin.

If your app is direct-to-prosumer, you need to think about whether you can really get to 100s of M of users or 10s of M at a really high price-point. Evernote is probably the best example and is still struggling with accelerating freemium growth.

With SMB deployment, you can charge a higher SAAS price-point plus drive more seats. Ideally, you can achieve this without a sales team like Slack and Github have demonstrated but realistically, you will need an inside sales team and ignoring this reality is why I’ve seen many productivity app developers fail.

3/ Replacing In a Category vs Creating a Category
Are you an app the SMB already pays for or something they don’t yet pay for? Slack, as an example is a new category in that SMBs did not previously pay for chat. However, if are a “Todo” app, you are probably competing with an already existing tool such a Jira that the SMB pays for. Getting a company to switch tools is hard and thus why I recommend targeting super-SMBs when replacing in a category.

4/ Create Lock-In
Most productivity apps aggregate some cloud data (files, CRM etc). In the PIM (email, calendar, address book) category, we aggregated email accounts (Google, Exchange, iCloud). Being an aggregator means we are the presentation layer. But without any content exclusively stored in our system, the user can switch presentation layers without penalty.

To create lock-in, some options:
(a) Store some content exclusively
(b) Require upfront customization such as Salesforce
(c) Introduce paid; this will be the best thing you can ever do and will improve all of your metrics
(d) Achieve network effect. Hard to pull of but if you get it, hold on to it!

5/ Be Pervasive
Productivity is a lifestyle and is integrated across personal and work. Although mobile-first is my recommendation, don’t discount laptop usage at the workplace. Apps must be avail on all screens otherwise you are destined to fail.

6/ Have a Macro Thesis
Product management in productivity is hard – there is no 80/20. Workflows are unique to each individual and attempting to change and behave like a coach is exceptionally hard except when managed down (eg everyone has to use Expensify). It’s best to embrace the existing workflow and improve while also maintaining a macro product thesis. Without a thesis, your resultant app will look like the Settings dialogue in Office.

7/ Don’t Be Too Smart
As I’ve written previously, I believe predictive intelligence will be a new layer on all apps. But in the productivity, trust is always the #1 feature. Failing to sync an email will be an immediate deal-breaker. Optimize on precision (accuracy) vs recall (# of results) and ask the user when unsure versus being too smart. Although most contact mergers are pretty good, the 1 out of 10 times they fail is why many don’t embrace.

Tech Discrimination

I recently posted this on my Facebook and it triggered quite a bit of discussion. I was borderline surprised to see at least 1 commenter write that they would intentionally bump PCs they saw at coffee shops – probably a bit extreme but certainly acknowledges the reality of tech. Whether it be your choice of laptop, smartphone or even apps – don’t the cool kids use Snapchat? I guess we all want to be cool again – see below repost from Facebook.

Per my FB post below, here are some of my notes on migrating from Windows to Mac.


(Reposting from Facebook, July 28, 2015)

So I’ve officially made the switch to Mac – yes, I’m like a decade behind my colleagues and almost embarrassed to write this. At Tempo, I justified using a Windows laptop because I had to test Exchange sync with our calendar but secretly it was because I was an Office and Outlook die-hard and I couldn’t bear making the switch off of Outlook (not to mention, I didn’t think Windows was that bad 🙂

Well now that Tempo is part of Salesforce and my laptop is entering it’s 3rd year, it’s time to make a switch. The change interestingly is less so because I care about switching to Mac but more so because of the “tech discrimination” I used to get using Windows. In the last month, I’ve caught-up with multiple investors and I’d ask the point-blank question, what do you think if someone pitches with a PC. Most said, “I don’t really care but my partner…” -> cop-out! Clearly you’re at a disadvantage if you pitching with a PC.

Independent of that, I can’t tell you how many times I used to get funny stares speaking at conferences whipping out a PC. It always took a little bit of miracle-work because Mac connectors to the projectors have become the default.

I also remember being asked once in an interview in ’07 if I was a Mac or PC user, ha! In any case, I have folded to the peer pressure and probably upgraded at the same time. Technology is meant to be replaced with better!

Good luck Microsoft with the Window 10 launch tomorrow! And hoping that you can fix the consumer sentiment but unfortunately, it’s often winner take all until the next tidal change.

PS I’m working on a lengthy blog post at my personal website on how I configured Fusion with OSX so I can keep Outlook 🙂 until they get Outlook 2016 on Mac in parity!