UpGuard
10 · Roadmap 30-60-90

Roadmap 30-60-90

A validation-first approach. Listen → Research → Refresh → Ship → Measure. Each phase builds on the previous one.
Days 1-14
Listen
Days 15-30
Research
Days 31-60
Refresh
Days 61-90
Ship
Q2+
Measure & iterate
Listen: stakeholder + customer + data + competitor audit
Research: synthesis, hypotheses, validated positioning
Refresh: website, sales enablement, content, messaging
Ship: new BOFU + middle-funnel assets, measurement setup
Measure & iterate: quarterly cadence, customer advisory board

Days 1-14 · Listening phase

Stakeholder interviews

What I do
  • CMO, Head of Product, Head of Sales, Head of CS – priorities, roadmap, what's blocking
  • Head of Vendor Risk product – what's coming in the release notes, what features are being prepared
  • 2-3 top AEs – what closes deals, what's blocking
  • Customer Success leads – what customers love, what they criticize
What I'm looking for
  • Misalignment between Marketing, Product, and Sales
  • Internal hypotheses about positioning and customer pain
  • What the team considers sales blockers vs. what the data actually shows

Customer voice – qual + quant

Qualitative
  • 8-12 interviews with champions (current, churned, lost deals)
  • 4-6 interviews with CISOs
  • G2 / Gartner Peer Insights reviews mining
Quantitative
  • Survey existing customers – what drove the purchase
  • NPS / CSAT data review
  • Support tickets – what breaks in onboarding
What I'm looking for
  • Real purchase triggers vs. team hypotheses
  • Barriers and drivers by segment
  • JTBD formulations in the customer's language

Sales call analysis

What I do
  • Listen to 30-50 sales calls in Gong / Chorus
  • Top objections by frequency of mention
  • Top competitor mentions (who actually comes up in deals)
  • What the champion tells the CISO in shared calls
  • Which proof points work (references, case studies, numbers)
What I'm looking for
  • A basis for an objection handling guide based on real data
  • The real competitor landscape vs. the one in the pitch deck
  • Messaging that works in the first 5 minutes of a discovery call

Data audit

HubSpot
  • Win/loss reasons for 30-50 closed deals
  • Deal velocity by segment
  • Source / medium attribution
  • PQL → SQL → SAL → SQO conversion rates
GA / Mixpanel
  • Traffic by page, bounce rate
  • Conversion funnel, drop-off points
  • Which assets in demo deals were touched
Email + sales artifacts
  • Open rates, CTR, replies – what works
  • Which segments reply, which don't
  • Which assets AEs send most often

Competitive audit

What I do
  • Deep audit of Bitsight / SSC / Black Kite / RiskRecon websites
  • Competitors' LinkedIn activity (posting patterns, engagement)
  • Analyst reports: Forrester Wave, Gartner MQ, GigaOM
  • Release notes / PRs from the last 6 months
  • SimilarWeb / Semrush – competitors' traffic and channels
What I'm looking for
  • Best practices in messaging that UpGuard can adopt
  • Gaps in competitor positioning that UpGuard can use
  • What category claims they make and how they justify them