← Redwood Software
Redwood Software role-play cheat sheet
For the mock cold call at the end of most SDR interviews.
What they sell, in one line
Automation software that runs and connects IT jobs, finance processes and business workflows across complex systems.
Who you'd be calling
IT operations leaders, heads of finance systems, CFO-office and controller teams, and automation or SAP leads at large enterprises.
Your opener
“Hi, this is Chris from Redwood Software. I know I'm calling out of nowhere. We help IT and finance teams automate the repetitive back-office work that eats up their time, and I wanted to ask where your team still does a lot by hand?”
Problems you solve for them
- Manual, scheduled tasks across many systems break and need babysitting
- Finance teams spend days on month-end close work
- Old job scheduling tools are hard to scale and maintain
Discovery questions to ask
- Which processes in IT or finance still depend on manual steps or lots of scripts?
- How long does your month-end close take, and where does it slow down?
- How do you schedule and monitor jobs across your systems today?
Objections they'll throw at you
“I only have a minute.”
→ Got it, one question then. Where does your team lose the most time on repetitive back-office work?
“We're not interested.”
→ Fair. Is automation already well covered, or is it just not the right time for a project like this?
“We already have an automation tool.”
→ Good, so you know the value. Does it handle both IT jobs and finance processes, or are some things still done by hand?
“Email me something.”
→ Sure. To send the right thing, is your bigger challenge on the IT side or the finance side?
Competitors worth knowing
Automic (Broadcom), BMC Control-M, ServiceNow
Interview tips for this company
- Redwood sells to both IT and finance, so practice adjusting your pitch depending on who picks up.
- Learn what 'workload automation' means in one simple sentence, like 'software that runs tasks automatically so people don't have to'.
Written from public information about Redwood Software to help you practice. Ask an insider what their role play looked like; it's the best prep there is.