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January 23, 2024

The Art of Marketing Leadership: Emily Singer

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Show notes

In this episode of Marketing Spark, Emily Singer, VP and Head of Marketing at Drift, joins Mark Evans to discuss her journey and experiences in marketing leadership.

The conversation covers the evolution of Drift's brand messaging and the complexities of marketing in a rapidly changing business environment.

Emily talks about the importance of the CEO-marketing leader relationship and the collaborative dynamic within Drift's senior management team, particularly during challenging market conditions.

She shares insights on aligning marketing strategies with company goals, the impact of AI in marketing, and the importance of internal communication in driving success.

From the conversation

Evolving the Drift brand for enterprise customers

Emily Singer is VP and Head of Marketing at Drift. She joined about two and a half years ago to build out the communications and branding organization. As the company moved toward a broader corporate and customer marketing approach, her role grew with it. In September, the CEO asked her to lead the entire marketing team, which she describes as exciting and humbling.

Her early brief came from her first interview with Drift founder David Cancel. Drift had built a scrappy, outspoken and at times controversial brand to break into and invent the conversational marketing space. As the product and strategy matured and Drift sold to more enterprise customers, the brand and messaging had to mature with them. Emily says that was a large part of her charter when she joined.

Running the leadership team as 'Team One'

Emily explains that CEO Scott Ernst gave the leadership team a principle called 'Team One.' He compares it to parents who need to be united and respectful of each other to get the outcomes they want for their children. At Drift, it means the leaders share ownership of five strategic growth initiatives, instead of treating go-to-market as a marketing job and the product initiative as a product job.

The idea was discussed at a November offsite north of Boston, where the newly formed team agreed on how to operate and what to hold each other accountable for. Day to day, the group meets for two hours every other week to review Tier One, Tier Two and Tier Three metrics. They share what is and is not working and solve challenges together.

The team also agreed to embrace productive conflict, including being willing to disagree and commit, so that leaders go to the market, the team and the board aligned. Emily comes from a communications background and calls internal communications one of the most undervalued levers in an organization. Regular one-on-ones between functional leaders decide what gets passed down to frontline managers and individual contributors.

"And we really err on the side of overcommunicating what our teams are focused on and what we're doing next."

Emily Singer

Working with the CFO and budgeting for brand and demand

Emily has seen more CFO involvement in marketing as macroeconomic conditions have tightened. At Drift, 2023 was the year of measurement, and that carried into 2024. She works with Tim Redfern, the CFO and COO, on making data-driven decisions. The team is now designing its marketing budget for fiscal year 2025, which starts in February. Scott makes sure those conversations do not happen in a silo, so the budget is viewed through the lens of the whole company and its fast-moving product roadmap.

At a macro level, next year's plan is roughly 25% brand spend and 75% demand spend. In 2023, Drift cut back on brand events that were less dollar-in, dollar-out. Emily says the 25% brand portion will need extra internal communication about how it pays off. She often uses Simon Sinek's gym analogy, where someone lifts their shirt after one workout and expects to see abs.

To show that brand work is paying off, Emily points to simple top-of-funnel signals such as engagement, organic site traffic and what Google Analytics shows. When exact attribution is not available, she relies on qualitative evidence such as customer feedback. She says measurement is the biggest challenge in winning support for brand, and she has worked under two CEOs who understood its value.

"Brand is very much like that. You have to commit to the long-term repetitive consistency."

Emily Singer

Reviewing campaigns and initiatives that miss expectations

Emily says the key to handling a miss is to have the conversation before it happens. Drift's leadership touch points happen daily, weekly and monthly, so the team can predict where things are going well and where they are not, and then remove obstacles together.

When something does not work, the team digs into the reason. Emily lists seasonality, the messaging and the offer as possible causes. The team relies on shared principles when it reviews a failure.

Some problems remain open. Emily gives the example of attributing marketing pipeline to expansion, where adoption, retention and expansion all have to work together with the customer team. She says there is no perfect answer yet, and the team keeps taking a collaborative, extreme ownership approach.

"We focus on attacking the problem and not attacking each other. We try to assume good intent, and there are large challenges that marketing teams are all trying to solve."

Emily Singer

Sales and marketing alignment and marketing leader tenure

Mark cited a survey putting the average Fortune 500 CMO tenure at 4.2 years. Emily says that in her experience, turnover comes mostly from a lack of alignment with the sales team, and then with the CEO. She also notes that marketing is an executive function women occupy more often than men, says that may play a part, and leaves it there.

She gives an example from a former company during COVID. Performance dipped for a quarter and fingers were pointed over what marketing could have contributed when sales fell. Emily says trust has to exist before a crisis, because when it is missing in good times, the breakdown shows up under pressure.

At Drift, Emily and sales leader Lee tell both teams that metrics are owned and shared. The company focuses on bookings and their effect on ARR, with the phrase 'one pipeline, one team.' Emily says the line between sales and marketing is rarely clear, since marketing may invite someone to an event while a salesperson does the legwork to close.

"We do not break down pipeline currently by attribution. We were spending way too much time in the last fiscal year trying to assign credit, for lack of a better word, to where sales was contributing, where marketing was contributing."

Emily Singer

Using AI at Drift and the trends Emily expects

Emily says Drift has been a pioneer in conversational AI for longer than many vendors claim. Internally, the marketing team uses its own platform, which Drift calls 'Org One' (Drift on Drift), including Bionic chatbots. That means moving from hundreds of playbooks toward one playbook, or zero, as they become bionic. The team also uses tools such as Jasper and ChatGPT.

After an Ask Me Anything session at a weekly marketing huddle, Scott challenged the team to take a leadership role on AI. He asked them to share results and the best tools at all-hands meetings.

Looking ahead, Emily cites a Gartner stat that 70% of a buyer's research is done before engaging a brand, so marketing owns more of the buyer journey. She expects account-based marketing to stop being the gold standard of personalization as AI makes one-to-one personalization possible. Citing Merkle data, she says vendors have largely failed to meet buyer expectations because of a lack of scale. Listeners can find Emily on LinkedIn or at @emccsinger, and can try the Bionic Chatbot Demo at drift.com.

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