Personas
Executive Levels
Email / Cold Calling Best Practices
Value Selling & Objection Handling
100

Name two common pain points for CX leaders that Grammarly addresses.

1. Big Three #1: Improve the customer experience. Delivering the best possible customer experience with fast and consistent support that resolves issues quickly will differentiate the brand, help retain customers, enhance brand reputation, and ultimately grow revenue.

2. Big Three #2: Enforce quality and compliance standards. Agent skill, English proficiency levels, and cultural differences in communication can be very diverse, and poor quality or inconsistent interactions risk brand reputation, customer churn, and future growth. Organizations need a way to efficiently onboard and upskill employees to consistently enforce these quality standards across their teams to deliver better customer experiences.

3. Big Three #3: Reduce costs. Customer Support is often seen as a cost center, and as a support organization scales to meet customer demand, they need to navigate how to deliver great customer experiences in a cost-effective way. This is especially important when methods to improve CX come at high costs, like hiring the most experienced agents with high levels of English proficiency, paying for courses to upskill agents’ English skills, hiring training staff, hiring floor managers or QA staff to oversee and ensure quality.

100

What are the title levels of propsects that we sell to here at Grammarly? 

Manager, Director, VP, and C-suite 

100

How long typically do cold emails get viewed for? 

Cold outreach emails only get viewed for ~9 seconds on average…so every second counts!

100

What does value-based selling prioritize?

The customer's needs and pain points!

100

Name two common pain points for Marketing leaders that Grammarly addresses.

1️⃣ Scale Content Production: Marketing content production and revision cycles are too slow, contain bottlenecks, and are difficult to scale

2️⃣ Effectively Capture Audiences: Developing compelling and high-quality content to capture audiences is extremely time-consuming

3️⃣ Ensure Brand Consistency: The customer experience is fragmented or inconsistent across brand touchpoints

100

What buying powers does a manager have?

Buying Power: Typically has an influence on purchasing decisions but rarely has the final say. They often make recommendations or act as gatekeepers

100

On average, how many cold call attempts does it take to connect with a lead?

On average, it takes 3 cold call attempts to connect with a lead!

100

What’s the key to building trust in value-based selling?

RESEARCH 

100

Name two common pain points for IT leaders that Grammarly addresses.

1️⃣ Maintaining a secure enterprise: The organization’s employees are leveraging unsanctioned AI tools in their day-to-day, putting the company’s information at risk. 

2️⃣ Maximize productivity and operational efficiency: IT teams are responsible for deploying and maintaining over 200+ tools for the Enterprise while also ensuring the tools the company uses meet everyone’s needs within an increasingly dynamic, global, and hybrid workplace. 

3️⃣ Being perceived as a cost center versus an innovation hub that partners in achieving business success: IT leaders want to lead with innovative technologies but are cognizant about time to value and business impact. They need help proving the value of any new technology.

100

T or F: Directors typically focus more on their team’s immediate needs than on company-wide strategy.

False - They focus on Strategic initiatives, long-term planning, and departmental performance.

100

How many words long should a cold email be, and why does length matter? 

Shorter emails get higher response rates: Emails between 50-125 words have a response rate of over 50%.

100

How can you handle a prospect saying, “Send me an email instead”?

What would you like to see in that email? 

200

What Features/Capabilities does Grammarly have that are important to IT Buyers?

- Security: Confidently bring generative AI and communication assistance to all your users, wherever they work, without sacrificing the security of your enterprise.

- Operational Efficiency: Save employees 13 hours (source) per week and reduce friction in collaborative work by delivering generative AI and communication assistance to your entire enterprise, wherever teams work.

- Competitive edge: Transform your business with a swift, company-wide integration of AI and propel it ahead of its competitors. With AI, you can become a leader in your industry and accelerate your business growth.

200

What is the best way to try to loop in other key stakeholders when speaking to a prospect with little to no buying power? 

- Asking for referrals 

- Using them as a champion 

- Collecting as much information as possible to help you create impactful messaging to their stakeholders 

200

What’s a strong call to action in a cold email, and why? (Give us an example) 

Let's find 30 minutes on Tuesday to dive into this a bit deeper and see if we can partner here to help you with these goals?

Create Urgency and give specific days and times to meet vs asking for a meeting in general will lead to better results!

200

When you are looking for an account to outbound in your book of business, what do you look for? 

  • Grammarly's ICP

  • Buying Signals (give examples)

  • New signups 

  • Funding 

  • Hiring rapidly
  • High Usage 
200

What Features/Capabilities does Grammarly have that are important to Marketing Buyers?

-Speed up content production and reduce revision cycles, with marketing teams (Supermetrics) cutting editing time by 75% and reinvesting time saved into other projects, creating immediate ROI.

- Advanced writing assistance to go beyond spelling and grammar and improve text for clarity, conciseness, tone, and more.

- Real-time guidance to enforce brand voice and style guidelines as teams write. Reinforce your brand in every customer touchpoint with AI that understands your company’s brand voice, style rules, and writing standards for a better, more unified customer experience, with some customers (Databricks) experiencing a 70% improvement in brand compliance.

200

How can we use usage to create urgency for our executive buyers? (Give us an example) 

Shows demand for Grammarly and you can highlight the potential impact of increasing adoption. 

200

What’s a common mistake to avoid when writing a follow-up email?

Asking for a meeting again or bumping your last email with no value added.

200

What research do you conduct once you decide to go after an account?

What to look at:

  • Company website 

  • Job postings

  • Company news 

  • 10 K/financial docs 

  • Tech crunch 

  • LinkedIn posts 

  • Zoominfo- What does the company’s leadership structure look like 

  • Outreach Account view - Crunchbase news/funding/past conversations

300

What is ITs role in the buying process and when do we want to engage with them? 

They act as gatekeepers, vetting vendors, influencing decision-making, and overseeing implementation to minimize risks and ensure seamless integration. Engaging IT early, addressing their priorities, and highlighting efficiency, security, and scalability are key to gaining their support in the buying process.


300

What is a VP of IT primary focus when evaluating a new technology?

ROI & SECURITY & Implementation 

300

You notice a prospect opens your emails multiple times but doesn’t respond. What should you do?

Try Another Channel! Reach out through a different medium, such as LinkedIn or a quick phone call, to spark a response and personalize the interaction.

Go after other contacts on their team. 

300

Explain to me our AC/DC Framework for Discovery and what parts are most important for BDRS. 

Always Prepare 

Control the convo 

Discovery 

Close 


Step 1️⃣: 🔍 Research and Preparation: Research Before Meeting

Step 2️⃣: 🗣️ Control the Convo: Set The Agenda

Step 3️⃣: 🪩 Discovery: The Discovery Phase

400

What does the day in the life look like for a Senior Diversity and Inclusion Program Manager? (Think Charlandra!)

  • Focussing on diversity and inclusion metrics, tracking progress against KPIs, and identifying areas for improvement.
  • Work on creating or enhancing programs that support underrepresented groups (e.g., mentoring programs, ERG initiatives, or leadership development workshops).
  • Leadership Updates: Prepare or present updates to leadership on the impact of D&I programs and make recommendations for future initiatives.
  • Meet with HR, Talent Acquisition, or Training teams to ensure D&I principles are embedded in recruitment, onboarding, and development processes.
  • Analyze feedback from employee surveys, program participation rates, or representation data to identify insights and trends.
400

What are the main focuses of the C-suite?

Focus: Overall business growth, profitability, and high-level strategy. Their concerns are more about the bottom line, scalability, and risk management.

400

What are 3 components to focus on when making a call? (What should you know before you dial - give examples of each) 

PERSONA → Understand their goals, challenges, and objectives. 

PERSONAL → Did they post something relevant on LinkedIn? What sort of content are they engaging in that would be relevant for your call with them?

WHAT’S HAPPENING AT THE COMPANY → ACCOUNT RESEARCH (website, job openings, funding, news articles etc)

400

Breakdown for us our objection handling framework. (The 7 steps) 

1) Pause, speak with calm authority 

2) Start with a question 

3) Validate 

4) Isolate 

5) Permission to address 

6) Reframe 

7) Unbiased resolution 

500

What does a VP of communication care about? (Think Shannon!) 

  • Ensuring all messaging aligns with the company’s values, mission, and vision.
  • Managing brand perception in the market to maintain trust and credibility.
  • positive media coverage, customer sentiment, and reputation metrics
  • Developing and executing a comprehensive communication strategy that supports business goals.
  • Building and amplifying the company’s thought leadership position in the industry.
  • Developing compelling narratives that differentiate the brand and showcase expertise.
  • Tracking the impact of communication strategies on brand awareness, engagement, and trust.
500

How would I change my pitch when speaking to a cx manager vs a director? Give us examples of what you would mention! 

CX Manager

Focus: Operational execution, improving team performance, and addressing immediate challenges in the day-to-day customer experience.

Key Points to Mention:

  • How Grammarly streamlines agent workflows or reduces response times (Time to resolution)
  • Enhancements that make their team’s daily work easier (reduces editing time & has snippets available for FAQs)
  •  KPIs directly tied to team performance (CSAT) 

CX Director

Focus: Strategic initiatives, customer retention, cross-functional alignment, and impact on business goals.

  • High-level impact on customer satisfaction and loyalty.
  • Customer Retention 
  • ROI and scalability of Grammarly
  • Data analytics to drive insights and strategic decision-making.



500

What does a cold call include? (Hint - think cold call framework)

Introductory Hook

  • Keep it short, focus on a relevant problem, and mention any referrals or mutual connections.

  • “Curiosity Build” - buy their next 7 seconds - they Why you/why now 

Qualifying Questions

  • Ask questions that encourage prospects to reveal their current situation and potential pain points.

  • Building upon your why you/why now - FIND THE PAIN

Value Statement 

  • The Grammarly of it - use what you found to now connect it back to how we can solve their problem with a specific, relevant value proposition. Example: “We helped [Similar Company] reduce [specific pain] by [percentage]. Does that sound like something you’d be interested in?”

CTA

  • Tie what you just heard back to why there should be a next step 

  • Provide an easy and direct next step. 

500

A Director of IT tells you "We are not currently evaluating new tools." How would you continue the conversation? 

"That’s completely valid. A lot of IT teams are focused on optimizing their current stack rather than adding new tools."

" I am curious When your team does evaluate new tools, what does that process typically look like?"'

" Mind sharing How you are approaching optimization—are you consolidating tools, improving integrations, or something else?" 


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