I’m Back in the Startup Game—Here’s Who and Why ...
I’ve joined this+that - Using AI to tackle the hidden productivity killer affecting every team.
Over the past few years, I've dedicated significant time to teaching customer development—specifically the Mom Test methodology—at universities, incubators, and accelerators across Europe. While running a coworking space can be time-consuming, I realised my passion remains deeply rooted in customer development and sales, particularly early-stage sales for tech startups navigating the challenging journey of bringing new ideas to market.
Through these experiences, I've observed how entrepreneurs often struggle with premature attachment to their initial idea, leading to difficulties in objectively validating if anyone wants it, acquiring those crucial first 10–20 customers, or pivoting quickly when necessary.
I'm excited to share that I've been helping an AI startup called this+that. I initially helped them build an MVP and secure initial funding, and now we have a MVP to show.
In my role at this+that, I'm focused on validating key assumptions around a productivity challenge we believe affects virtually every organisation: unplanned work.
Imagine an AI that ensures you never miss a task! It scans project conversations across email, Slack, meetings, and other platforms to come, identifying both issues and unplanned tasks, and connects them to your project management tool. From Trello, Jira, monday.com, Asana and many more.
Sign up while it’s free to trial it here.
The Hidden Challenge of Unplanned Work
Most organisations have become proficient at managing and optimising planned work in business productivity. Tools like ClickUp, Monday.com, Asana, Trello, and Jira excel in helping teams break down structured projects into clear tasks, timelines, and accountability checkpoints. Yet, despite these tools' sophistication, is there a critical productivity leak affecting nearly every organisation? —unplanned work?
We categorised unplanned work into two distinct types. The first type includes tasks that haven't been captured and integrated into project management tools. These are tasks that teams are aware of but fail to document properly—perhaps forgotten, not updated, or buried in emails and communications that don't translate into clear, actionable items. This type of unplanned work is estimated to represent 30-40% of overall unplanned tasks.
The second type, estimated at roughly 50% ? is the more disruptive "silent disruptor." Bottlenecks in the company. These are critical, unforeseen issues that emerge spontaneously through communication channels such as Slack, meetings, and emails. This category encompasses urgent regulatory changes, unexpected customer requirements, emergent market conditions, or internal conflicts—complex problems that don't neatly fit into predefined task lists and typically remain hidden until they cause significant disruptions or project failures.
How Businesses Currently Address (or Don't Address) Unplanned Work
Most productivity platforms are designed for planned work, assuming clear task identification from the outset. Hoop recently raised an astonishing $5 million to address part of this by scanning for tasks that inadvertently get missed in standard project management software. Yet, Hoop's approach is primarily transactional, identifying isolated tasks rather than contextual, communication-driven issues.
On the other hand, enterprise search platforms like Glean offer powerful solutions to retrieve organisational information when a user actively queries it. However, their reactive, search-based approach assumes awareness of an issue's existence—something unplanned work frequently lacks.
Hot Topics: Where Communication Meets Action
A deeper, more disruptive aspect of unplanned work exists: critical issues and decisions hidden within everyday communication. These issues we are calling "hot topics" are not merely overlooked tasks—they represent vital insights, challenges, or opportunities that require collective attention and swift resolution. This is where this+ that AI is validating. Our platform uses AI-driven technology to proactively surface these "hot topics" by continuously scanning your organisation's communications, helping you identify and prioritise critical issues before they escalate or derail your projects. Rather than passively awaiting queries, this proactively alerts managers and leaders about these significant hidden matters, empowering teams to tackle challenges head-on and enhance organisational agility.
Looking for Early Adopters and Researchers
We believe deeply in collaboration and co-creation. We understand that the best solutions are built when real-world users provide active feedback, shaping the tool based on genuine organisational needs. We're seeking early adopters, beta testers, and researchers passionate about productivity, organisational efficiency, and communication effectiveness.
We are inviting leaders, project managers, product leaders, and sales executives who face daily inundation from communications and wish to unlock insights buried in their emails and messaging platforms. We want to learn about your current challenges, existing solutions, and ideal outcomes when addressing unplanned work.
If this problem resonates with you, feel free to email me, chat or explore it further here.
Gerald