How I Buy - Amanda Richardson, Chief Data and Strategy Officer, HotelTonight - - Relationship Intelligence for Sales

How I Buy – Amanda Richardson, Chief Data and Strategy Officer, HotelTonight

By Steve Woods in #HowIBuy


You would expect that the executive running data and strategy functions of a hot, fast growing company would be intense, practical, no BS, and incredibly smart. Amanda Richardson does not disappoint.

I chatted with Amanda for Nudge’s #HowIBuy series, and I was impressed with her ability to jump between areas of her buying process that were rigorously defined and areas that were fuzzy and gut hunch based, with the same ease and clarity on her approach in both areas.

Here are Amanda’s views on buying, hopefully you’ll enjoy them as much as I enjoyed the conversation:

Thanks for the time Amanda. First tell us a little about HotelTonight to set some context of who HotelTonight is as a company and what you provide.

HotelTonight is the best place to book a hotel room. We’ve got the best values on beautiful properties throughout the world. In terms of size, we’re around 300 people across 6 offices, so not really startup, but not a big enterprise.

And in your role, what do you generally spend money on throughout the year?

As Chief Data & Strategy Officer, I run all data and strategy efforts. That means three main areas. Our engineering spend, data warehousing, and ETL are under me. Dashboarding and data visualization forms another main area of spend. Strategy and research forms the third big area, whether it’s one-off reports or data services.

First let’s talk about how you discover new ideas and tools. How do ideas make their way into your world?

I find out about new things really in one of two ways. Both ways are really word of mouth – someone mentions a tool that has really solved a problem. The most common is someone on my team, and the second most common is someone in my network that I respect.

As one recent example, we selected a new tool in just one week. We were struggling with our current vendor and a one of the folks on the team had worked with Tableau at a past job and had a good experience. We knew what worked, so we made the switch quickly. As a second example, we had inherited an old ETL tool and when one of the folks on our team asked their friends, Alooma came highly regarded. Those recommendations put those vendors into the lead in the evaluation, and we ultimately selected both options.

And with all the possible things to focus on, how do you decide on what’s “now” vs “later” in your priorities?

This is all about how big the problem is. I don’t think there’s any formal methodology, but since there’s always cool stuff out there, we need to be pretty choosy about what we invest our time in. If it’s a tool that is failing us, it’s more of a ‘painkiller’ situation, so we’ll move quickly. For new and improved ideas like new data sources or consulting, it will generally need to wait for a new budget cycle or we’ll be swapping out an existing solution. I always ask how essential something is and if we can live without it – because we probably have been.

My budget is generally quite specific about where the money is allocated to at the beginning of the year. There can be some ability to swap money around within a bucket, such as money allocated to consultants on a particular initiative, but outside of that, I try to create a plan and stick to it rather than getting distracted by shiny objects or spontaneous ideas. (Yes, this is ironic for a company that promotes spontaneous travel.)

Once you’ve started working on an area, how does your decision process work?

Our internal process is pretty standard, I think. I ask the team for a proposal with all the details of what, why, and how they are planning to use the proposed solution. Creating this internal story involves a lot of reaching out to vendors and other customers to gather data, understand processes, and test assumptions.

We’ll look for references, but I’m explicit that the team find references that were not provided by the salesperson. I discount those 100% out of the gate. The team member who is putting together the proposal will often get quite a bit of help from their salesperson as they pull together the details, but it’s on our process and timeline, not the salesperson’s.

Given this process, what can the best salespeople do to stand out?

For me the best salespeople are not only responsive and helpful, but also human. They own what their company does do well and what they don’t do well. I find that if a person does not admit what they don’t do well, I don’t trust what they claim to do well.

How has buying changed in the last decade?

We move much faster now. I think it’s because the switching costs are much lower, so we’re able to trust the team a lot more, make decisions faster, and if we make a mistake, revisit. There is much less of the detailed RFP-style diligence nowadays with matrices of feature checklists as they are not as needed in this faster-paced decision environment. No one ever read those anyway.

What part does your network play in how you learn and evaluate new ideas?

I talk shop with my network all the time. I’ll talk with them about what is interesting, good, and bad. Unless I can feel the pain myself it generally doesn’t surface as a priority for me. However, there’s often a long ‘fermentation’ process; if I hear of the same tool solving the same problem a bunch of times, it begins to gain a foothold, and I’m more aware of that problem as a potential priority.

I consider myself a pretty sophisticated buyer, but I’m definitely not immune to marketing, so it’s certainly possible that a marketing touchpoint or two adds to that perception that a solution is commonly used.

What do you find is the biggest mismatch between what you need and how salespeople sell?

I’d have to say it’s the emails. I probably get 15 or 20 every single day. I’ve seen all the common gimmick, “my CEO wants to meet with you”, “company ABC saved X%”, etc. I delete them within a second – I don’t open, I don’t even scan.

The other thing that, perhaps counterintuitively, I find to be a turn-off is an attempt to reference companies in our industry like Expedia and Priceline. We have a genuine belief that there’s a better way to operate within our industry – the way that the larger players have operated is not how we want to operate. I’m much more responsive to stories of best-of-breed organizations in other industries.

I also find that efforts that center around free stuff and expensive dinners rubs me the wrong way. I have a family life and the offer of box seats at a Giants game or dinner and drinks is insensitive to my time constraints. If you have that much extra money in your marketing budget, I want a price cut.

Thanks for great insights Amanda, I got a lot out of our conversation, and I hope that everyone reading this does too!

Steve Woods
CTO and Co-Founder
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