How to reboot your outbound sales engine during a GTM Transformation

Guest: Arianne Riddell, Chief Sales Officer at Personal Group (ex-LinkedIn, BBC, Feefo)
Host: Matt Milligan, Sales Performance Podcast

TL;DR — Key Takeaways

• Transformation is universal right now—across sectors, sizes and geographies—and sales teams feel the pressure first.
• Values drive behaviour. Pace, Passion, Professionalism (Personal Group) act as a decision filter for execution and culture.
• Your 30/60/90 won’t go to plan. Expect to mix learning, doing and influencing from day one.
• Rebuild the foundations: process, narrative (benefits > product), enablement stack (e.g., Salesloft, Walnut, Salesforce), and leadership credibility.
• Outbound is the controllable lever. Move teams from inbound-reliant to outbound-confident with clear KPIs, coaching and knowledge-sharing.
• Customer Success must be commercial. Use a top-down and bottom-up framework to drive expansion.
• Channel mix matters, but context wins. Phone still works—especially when supported by brand and targeted outreach.
• Lead with respect: “Love them up or love them out” when vision and behaviours don’t align.

“It’s tough out there”: Why Transformation Is Everywhere

Economic and regulatory headwinds across the UK and US are forcing organisations to restructure, re-think propositions, and re-energise teams. Arianne Riddell sees the impact most acutely in sales: keeping teams focused, motivated and performing amid constant change is now a leadership superpower.

This isn’t only a start-up story. From VC-backed scale-ups to Big Tech incumbents, transformation is now the default operating environment.

People-First Leadership Starts with Values That Actually Guide Work

Arianne credits her leadership grounding to LinkedIn’s hypergrowth era, where clear values, mission and culture were embedded into every decision. At Personal Group, three values—Pace, Passion, Professionalism—operate as daily decision filters for rewards, recognition and execution.

“It gives people really clear focus on what’s expected and how to show up.”

When values are alive (not wall art), they accelerate alignment, clarify trade-offs, and give managers a shared language for coaching.

Navigating Resistance: “Love Them Up or Love Them Out”

New vision and new ways of working won’t fit everyone—especially tenured team members used to legacy models.

Arianne’s approach:

1. Over-communicate the ‘why’. Map changes to concrete business goals; repeat often.
2. Make it personal. Show individuals how the change benefits their growth and career.
3. Be respectful and candid. If alignment doesn’t come, help people make their “next play”.

As one leader told Matt: “We’re going to love them up or love them out.” That means investing in people to succeed—and being humane if it’s not the right fit.

The First 90 Days (In Reality)

Forget the neat 30/60/90. In practice, you’ll learn, build and influence simultaneously.

Arianne’s priority stack at Personal Group:

• Process optimisation: Define an end-to-end sales process and tighten accountability.
• Narrative shift: Move from product-led to benefit-led selling (what customers care about, not feature tours).
• Enablement stack: Implement Salesloft (day management & AI surfacing priorities), Walnut (reliable, personalised demo experiences), and Salesforce (track leading indicators and pipeline truth).
• Hiring & structure: Recruit a Head of New Business and SDRs to diversify skills and execution capacity.
• Collateral and training: New creds deck, 101s, and cross-functional partnerships with Marketing.

The payoff? Incremental wins compound. New decks land better, messaging differentiates vs. “feature-heavy” incumbents, reps manage days more effectively—and pipelines respond.

Data-Led Talent: Replicate What Works

When Arianne arrived, data hygiene was thin. Step one: instrument the basics to see reality.

Track at minimum:

• Lead → Opportunity conversion
• Opportunity → Win conversion
• Deal cycle length
• Inbound vs. Outbound performance
• Rep-level trends on the above

This visibility enables pattern recognition (what the top cohort does) and replication (enable others with the same cadences, talk tracks and behaviours).

From Inbound-Dependent to Outbound-Confident

Many teams have enjoyed “the glory days” of leads flying in. That era is gone for challengers in commoditised markets.

Arianne’s outbound motion:

• Set clear KPIs and inspect consistently (activity and conversions).
• Coach the skill, not just the numbers: role-plays, talk tracks, objection patterns.
• Share what works across verticals and personas; templatise winning cadences.
• Mindset shift: outbound is the only lever reps fully control. Marketing is a partner, not a crutch.

“If you do it properly—with smart support—outbound works.”

Make Customer Success Truly Commercial

Expansion isn’t accidental. Arianne runs CS with explicit cross-sell, upsell and land-expand accountability, powered by a top-down and bottom-up strategy:

Top-down:

• Identify products that resonate, drive margin, or increase stickiness.
• List every client missing those products.
• Enable with collateral + campaigns and call sequences—don’t wait for QBRs.

Bottom-up:

• For each account, map business priorities & outcomes.
• Align specific products to known challenges and clear value.
• Trigger targeted outreach and executive alignment.

Run both at pace, measure, and iterate.

Channel Mix: Does Phone Still Work?

Short answer: yes—when context supports it. Cold calls are far more effective when surrounded by:

• Brand familiarity (so the name rings a bell), and
• Warm-up touches (email, LinkedIn, value snippets).

Arianne’s experience: phone often unlocks the next step, especially when emails have primed relevance. Persona and market dynamics matter—test, learn, adapt.

Build a Test–Learn–Iterate Culture

Transformation is a moving target. Arianne expects 10–15% of experiments to work—which is enough to win if you move quickly.

How to operationalise:

• Short feedback loops: weekly reviews of activity → conversion.
• Small bets, clear hypotheses: know what “good” looks like before you launch.
• Celebrate adoption and outcomes, not just ideas.
• Codify wins (playbooks, enablement) and retire what lags.

Practical Checklists

Sales Foundations Sprint (30–45 days)

• Define buying stages, entry/exit criteria, and MEDDICC/BANT (as relevant)
• Rebuild narrative: outcomes, proof, differentiation; kill feature sprawl
• Enablement in place: Salesloft/Walnut/Salesforce configured for leading indicators
• New creds deck + 101s; objection library; talk tracks
• SDR motion live with persona-specific cadences
• Weekly pipeline operating rhythm (by role + deal review rules)

Outbound Habits That Stick

• KPI ladder: activities → connects → meetings → SQOs → wins
• Daily call blocks + call coaching; call openers tested
• Multithreading standards (stakeholder count per opportunity)
• Sequence hygiene: A/B subject lines, CTAs, value assets
• Team show-&-tell: reuse what works across segments

CS Expansion Plays

• Top-down product gaps list by account
• Bottom-up account plans with mapped outcomes
• Monthly expansion blitz (calls + exec notes + proof points)
• Measure attach rates, expansion velocity, GRR/NRR lift

Leading with Credibility and Care

Early leadership wins come from showing you can do the work, building cross-functional trust, and being crystal-clear on standards. Pair that with respect and empathy, and you’ll keep more people “loved in”—and help others find the right next chapter when needed.

About the Guest

Arianne Riddell is Chief Sales Officer at Personal Group. Her career spans media, LinkedIn’s hypergrowth years, SaaS leadership at Feefo, and now a people-first transformation remit across new business, customer success, partnerships and implementation.

Listen & Connect

• Podcast: Sales Performance Podcast — weekly playbooks from top CROs/CSOs.
• Connect with Arianne: LinkedIn.
• Enjoyed this conversation? Subscribe and drop a comment with your biggest transformation challenge.

Bonus: Prompt Starters for Your Team Meeting

• Which value do we most live this quarter—Pace, Passion or Professionalism? Which one needs a push?
• What’s our one outbound behaviour we’ll all commit to for the next 2 weeks?
• Which product has the highest expansion potential and which 10 accounts will we call this week?
• What’s one enablement friction we’ll remove in the next 5 days?